Home / Articles / Uronic acids: synthesis and reactions

Uronic acids: synthesis and reactions

Viktor Arkadievich Timoshchuk 1
Viktor Arkadievich Timoshchuk
1 Belarusian State University, Department of Chemistry, Minsk
Published 30 November 1994
Communication , Volume 64, Issue 7, 675-703
13
Share
Cite this
GOST
 | 
Cite this
GOST
Timoshchuk V. A. Uronic acids: synthesis and reactions // Russian Chemical Reviews. 1995. Vol. 64. No. 7. pp. 675-703.
GOST all authors (up to 50)
Timoshchuk V. A. Uronic acids: synthesis and reactions // Russian Chemical Reviews. 1995. Vol. 64. No. 7. pp. 675-703.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1995v064n07ABEH000169
UR - https://rcr.colab.ws/publications/10.1070/RC1995v064n07ABEH000169
TI - Uronic acids: synthesis and reactions
T2 - Russian Chemical Reviews
AU - Timoshchuk, Viktor Arkadievich
PY - 1995
DA - 1994/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 675-703
IS - 7
VL - 64
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1995_Timoshchuk,
author = {Viktor Arkadievich Timoshchuk},
title = {Uronic acids: synthesis and reactions},
journal = {Russian Chemical Reviews},
year = {1995},
volume = {64},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1995v064n07ABEH000169},
number = {7},
pages = {675--703},
doi = {10.1070/RC1995v064n07ABEH000169}
}
MLA
Cite this
MLA
Timoshchuk, Viktor Arkadievich. “Uronic acids: synthesis and reactions.” Russian Chemical Reviews, vol. 64, no. 7, Nov. 1995, pp. 675-703. https://rcr.colab.ws/publications/10.1070/RC1995v064n07ABEH000169.
Views / Visits / Downloads
29 / 29 / 9

Abstract

The review describes the methods of synthesis of uronic acids involving both the catalytic oxidation of sugars and their oxidation by nonspecific oxidants. The principal paths in the transformations of uronic acids and their derivatives, characteristic of compounds of this class, which make it possible to synthesise new compounds that are otherwise difficult to obtain are considered. The bibliography includes 217 references.

References

1.
THE PREPARATION OF D-ARABOPENTURONIC ACID AND D-THREO- AND D-ERYTHRO-TETRURONIC ACIDS
2.
The Reduction of Tartaric Acid1
Lucas H.J., Baumgarten W.
Journal of the American Chemical Society , 1941
5.
An unusual carbo-carbon bond cleavage by KMnO4-CuSO4 Reagent
Mandal S.B., Achari B., Ghosh Dastidar P.P.
Tetrahedron Letters , 1993
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
Novobiocin. VIII. The Configuration of Noviose
Walton E., Rodin J.O., Stammer C.H., Holly F.W., Folkers K.
Journal of the American Chemical Society , 1958
12.
Modellversuche zur Theorie der alkoholischen Gärung, II.: Die Oxydation der Monoaceton‐3.6‐anhydro‐ d ‐glucose
13.
Synthesen von Xyluron- und Riburons�urederivaten
Weidmann H., Oberwalder H.W., Wildschek E., Schwarz H.
Monatshefte fur Chemie , 1972
14.
Holý A., Votruba I., De Clercq E.
Collection of Czechoslovak Chemical Communications , 2011
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
THE PREPARATION OF L-LYXURONIC ACID, L-LYXOSE, AND 5-DEOXY-L-LYXOSE
Hulyalkar R.K., Perry M.B.
Canadian Journal of Chemistry , 1965
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
Funktionelle D‐Lyxuronsäure‐Derivate aus D‐Mannose
Schmidt R.R., Hermentin P.
Chemische Berichte , 1979
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
Synthetic studies on biologically active natural products by a chemicoenzymatic approach
Ohno M., Ito Y., Arita M., Shibata T., Adachi K., Sawai H.
Tetrahedron , 1984
23.
Eine neue ungesättigte Anhydro‐glucose
Helferich B., Himmen E.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1928
24.
289. The synthesis of conjugated hexuronic acids
Marsh C.A.
Journal of the Chemical Society (Resumed) , 1952
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
27.
Notes
Overend W.G., Shafizadeh F., Stacey M., Vaughan G., Ongley P.A., Burnell R.H., Taylor W.I., Bowen H.J., Richards G.N., Gerrard W., Tolcher P., Collins R.F., Evans E.A., Whalley M., Jones J.K., et. al.
Journal of the Chemical Society (Resumed) , 1954
29.
Synthesis of Phenyl β-D-Glucopyruronoside1
Tsou K., Seligman A.M.
Journal of the American Chemical Society , 1953
30.
A Practical Synthesis of D-Glucuronic Acid through the Catalytic Oxidation of 1,2-Isopropylidene-D-glucose2
Mehltretter C.L., Alexander B.H., Mellies R.L., Rist C.E.
Journal of the American Chemical Society , 1951
31.
L-Glucose. A convenient synthesis from D-glucose
Szarek W.A., Hay G.W., Vyas D.M., Ison E.R., Hronowski L.J.
Canadian Journal of Chemistry , 1984
32.
Selective Catalytic Oxidation of Carbohydrates, Employing Platinum Catalysts
33.
The Preparation of d-Galacturonic Acid from d-Galactose1
Sell H.M., Link K.P.
Journal of the American Chemical Society , 1938
34.
117. Preparation of d-mannuronic acid and its derivatives
Ault R.G., Haworth W.N., Hirst E.L.
Journal of the Chemical Society (Resumed) , 1935
35.
SYNTHESIS OF THE HEXURONIC ACIDS
Niemann C., Link K.P.
Journal of Biological Chemistry , 1933
36.
158. Synthesis of uronic acids. Part III. d-Mannuronic acid
Stacey M., Wilson P.I.
Journal of the Chemical Society (Resumed) , 1944
37.
322. The synthesis of uronic acids
Stacey M.
Journal of the Chemical Society (Resumed) , 1939
38.
341. Deoxy-sugars. Part XXI. Synthesis of some derivatives of 2-deoxy-D-galacturonic acid
Overend W.G., Shafizadeh F., Stacey M.
Journal of the Chemical Society (Resumed) , 1951
39.
39
V. F. Gachkovskii
Biofizika , 1959
42.
Anomalous oxidative dimerisation of some carbohydrate primary alcohols with CrO3,2C5H5N
Yunker M.B., Fraser-Reid B.
Journal of the Chemical Society Chemical Communications , 1975
43.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
48.
Synthesis1 of L-Iduronic Acid and an Improved Production1 of D-Glucose-6-C14
Shafizadeh F., Wolfrom M.L.
Journal of the American Chemical Society , 1955
51.
Synthesis of methyl α- and β-D-gulopyranosiduronic acids
Anthonsen T., Sallam M.A.
Carbohydrate Research , 1980
55.
Synthesis of 5-deoxy-D,L-,ribo-hexofuranuronate derivatives via 7-oxanorbornanones
Schmidt R.R., Beitzke C., Forrest A.K.
Journal of the Chemical Society Chemical Communications , 1982
60.
Clarification of the mechanism of rearrangement of enol silyl ether epoxides
Rubottom G.M., Gruber J.M., Boeckman R.K., Ramaiah M., Medwid J.B.
Tetrahedron Letters , 1978
62.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
63.
63
1930
70.
70
N. Bubnov
Biofizika , 1960
71.
Novel application of alkyl dihalogenoacetates; chain extension with an α-ketoester unit of carbohydrates
Coutrot P., Grison C., Tabyaoui M., Czernecki S., Valery J.
Journal of the Chemical Society Chemical Communications , 1988
73.
Zinc-iron couple induced conjugate addition of alkyl halide derived radicals to activated olefins
Blanchard P., Da Silva A.D., El Kortbi M.S., Fourrey J.L., Robert-Gero M.
Journal of Organic Chemistry , 1993
74.
75.
Reaction of the methyl 2,3-anhydro-D-ribofuranosides with nuleophiles
Austin P.W., Buchanan J.G., Oakes E.M.
Chemical Communications (London) , 1965
81.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
82.
82
G. P. Brin
Biokhimiya , 1957
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
Some synthetic inhibitors of β-D-glucosiduronase
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
91.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
98.
Synthesis of 2-amino-2-deoxy-d-mannuronic acid and some derivatives thereof
Kundu N.G., Crawfor J.F., Prajsnar B., Reed E.J., Rosenthal S.
Carbohydrate Research , 1970
100.
The structure of the glycolipid components of the aridicin antibiotic complex
Jeffs P.W., Chan G., Sitrin R., Holder N., DeBrosse C.
Journal of Organic Chemistry , 1985
101.
Synthesis of 2-acetamido-2-deoxyhexuronic acids with the d-gluco, d-manno, and d-galacto configurations
102.
2-Amino-2-deoxy-D-xylose and 2-Amino-2-deoxy-D-ribose and Their 1-Thioglycofuranosides1
103.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
104.
dl-Isoserine and related compounds
Williams T.M., Crumbie R., Mosher H.S.
Journal of Organic Chemistry , 1985
106.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
107.
A New Reductone derived from D-Glucuronolatone, 3-Keto-4, 5-dideoxy-trans-4, 5-dehydroglucuronic Acid
Ishidate M., Kimura M., Kawata M.
Chemical and Pharmaceutical Bulletin , 2011
108.
Quantitative Estimation of the Fehling Reaction of 1-O-Protected Uronic Acids
Yoshimura J., Hashimoto J., Ando H.
Bulletin of the Chemical Society of Japan , 1973
109.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
110.
Structure and total synthesis of chryscandin, a new antifungal antibiotic
Yamashita M., Kawai Y., Uchida I., Komori T., Kohsaka M., Imanaka H., Sakane K., Setoi H., Teraji T.
Tetrahedron Letters , 1984
112.
3-Oxoglucuronic Acid. III. Synthesis of 3-Amino-3-deoxy-D-allouronic Acid
TSUJI A., KINOSHITA T., MAEDA M.
Chemical and Pharmaceutical Bulletin , 2011
114.
The synthesis of racemic 4-deoxyneosamine C
Banaszek A., Zamojski A.
Carbohydrate Research , 1976
115.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
116.
Synthesis of two 3-amino-2,3-dideoxyhexuronic acid derivatives
Horton D., Weckerle W., Winter B.
Carbohydrate Research , 1979
117.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
118.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
125.
Chain elongation of sugars with ethyl isocyanoacetate
Bischofberger K., Brink A.J., De Villiers O.G., Hall R.H., Jordaan A.
Carbohydrate Research , 1978
126.
Synthesis of C-glycosyl compounds. Part 1. Reaction of ethyl isocyanoacetate with 2,3:5,6-di-O-isopropylidene-D-mannono-1,4-lactone
Hall R.H., Bischofberger K., Eitelman S.J., Jordaan A.
Journal of the Chemical Society Perkin Transactions 1 , 1977
130.
Preparation of analogues of the carbohydrate moiety of the polyoxins
Bischofberger K., Brink A.J., de Villiers O.G., Hall R.H., Jordaan A.
Journal of the Chemical Society Perkin Transactions 1 , 1977
131.
Synthesis of fluorinated branched-chain sugars
Bischofberger K., Brink A.J., Jordaan A.
Journal of the Chemical Society Perkin Transactions 1 , 1975
132.
Branched-chain glycosyl α-amino acids
Rosenthal A., Richards C.M., Shudo K.
Carbohydrate Research , 1973
133.
Glycosyl α-amino acids
Rosenthal A., Richards C.M.
Carbohydrate Research , 1973
134.
Synthesis of an analog of the nucleoside moiety of the polyoxins
135.
Synthesis of an analogue of the polyoxins
Brink A.J., Coetzer J., De Villiers O.G., Hall R.H., Jordaan A., Kruger G.J.
Tetrahedron , 1976
136.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
DERIVATIVES OF GLUCURONIC ACID
Goebel W.F., Babers F.H.
Journal of Biological Chemistry , 1933
140.
Uronoside Formation Catalyzed by Cation Active Resin1
Osman E.M., Hobbs K.C., Walston W.E.
Journal of the American Chemical Society , 1951
141.
DERIVATIVES OF GLUCURONIC ACID
Goebel W.F., Babers F.H.
Journal of Biological Chemistry , 1935
142.
Selective Methanolysis of Lactone Rings in Some Acyl Carbohydrates
MATSUNAGA I., TAMURA Z.
Chemical and Pharmaceutical Bulletin , 2011
143.
Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide.
Chernyak A.Y., Antonov K.V., Kochetkov N.K., Padyukov L.N., Tsvetkova N.V.
Carbohydrate Research , 1985
146.
Reaktionen der glucuronsäure
Dax K., Weidmann H.
Carbohydrate Research , 1972
147.
Reaktionen der Glucurons�ure, 4. Mitt.
Weidmann H., Dax K., Wewerka D.
Monatshefte fur Chemie , 1970
149.
Selective benzoylation of methyl (methyl α-D-galactopyranosid)uronate
Gill P.L., Horner M.W., Horner L., Richardson A.C.
Carbohydrate Research , 1971
151.
152
W. Albert
Trans. Electrochem. Soc. , 1943
152.
153
1899
153.
154
Friedl.
154.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
155.
Reactions of D-Glucofuranurono-6,3-Lactone
Dax K., Weidmann H.
Advances in Carbohydrate Chemistry and Biochemistry , 1976
156.
Syntheses of Some Derivatives of D-Glucuronic Acid
Irimajiri T., Yoshida H., Ogata T., Inokawa S.
Bulletin of the Chemical Society of Japan , 1970
158.
A facile synthesis of 1,2,-o-isopropylidene-β-L-idofuranurono-6,3-lactone
Csuk R., Hönig H., Nimp J., Weidmann H.
Tetrahedron Letters , 1980
159.
A Simple Synthesis of L-Idose
BLANC-MUESSER M., DEFAYE J.
Synthesis , 1977
160.
A novel synthesis of 5-thio-D-glucose
Driguez H., Henrissat B.
Tetrahedron Letters , 1981
162.
Methyl α- and β-l-gulofuranosidurono-6,3-lactone
Macher I., Dax K., Inselsbacher H., Weidmann H.
Carbohydrate Research , 1979
163.
164
1917
164.
165
Friedl.
165.
Synthesis of pseudo-C-nucleosides
Rauter A.P., Figueiredo J.A., Ismael I.M.
Carbohydrate Research , 1989
167.
Elimination Reaction ofAldehydo-D-glucurono-6,3-lactone Derivatives
Itoh H., Aoki K., Matsumoto T.
Bulletin of the Chemical Society of Japan , 1985
168.
Tri-O-acetyl-β-D-glucopyranurono-6,1-lactone
Fry E.M.
Journal of the American Chemical Society , 1955
170.
171
Friedl.
172.
Funktionelle Riburonsäurederivate
Schmidt R.R., Jung K., Hermentin P.
Chemische Berichte , 1978
174.
175
I. Mayer
1966
176.
β-Eliminative Degradation of Carbohydrates Containing Uronic Acid Residues
Kiss J.
Advances in Carbohydrate Chemistry and Biochemistry , 1974
178.
179
Chem. Abs. , 1947
179.
Unsaturated carbohydrates. Part 22. Alkenes from 5-bromohexopyranose derivatives
Blattner R., Ferrier R.J., Tyler P.C.
Journal of the Chemical Society Perkin Transactions 1 , 1980
181.
An Allylic Rearrangement Arising from Reaction of Fluoride Ion and A 3-Chloro, 4,5-Unsaturated Uronate Derivative
Kiss J., Wyss P.C., Flesch G., Arnold W., Noack K., Schönholzer P.
Journal of Carbohydrate Chemistry , 1985
182.
Synthesis of uracil nucleosides of D-xyluronic acid derivatives
Akhrem A.A., Timoshchuk V.A., Mikhailopulo I.A.
Carbohydrate Research , 1975
183.
184
F. Haurowitz
"The Chemistry and Function of Proteins" , 1965
185.
186
Chem. Abs. , 1956
186.
187
1954
188.
Selective deacetylation of anomeric sugar acetates with tin alkoxides
Nudelman A., Herzig J., Gottlieb H.E., Keinan E., Sterling J.
Carbohydrate Research , 1987
193.
Holý A.
Collection of Czechoslovak Chemical Communications , 2011
194.
195
M. Allen
J. Chem. Soc. , 1961
195.
5′-substituted-5′-deoxy nucleosides
Baker J.J., Mian A.M., Tittensor J.R.
Tetrahedron , 1974
197.
Sodium Borohydride as a Reducing Agent in the Sugar Series1
Wolfrom M.L., Anno K.
Journal of the American Chemical Society , 1952
200.
Action of Grignard reagents on hexuronic esters and attempted dehydration of tertiary alcohols to give hex-5-enopyranosides
Aspinall G.O., Igarashi O., Krishnamurthy T.N., Mitura W., Funabashi M.
Canadian Journal of Chemistry , 1976
201.
Glycosiduronic Acids and Related Compounds
Keglevic D.
Advances in Carbohydrate Chemistry and Biochemistry , 1979
202.
203
L. Andrieux
Compt. rend. , 1929
204.
A facile O-glycosidation using stannic chloride.
HONMA K., NAKAZIMA K., UEMATSU T., HAMADA A.
Chemical and Pharmaceutical Bulletin , 2011
205.
Stereoselective glycosidations of uronic acids
Schmidt R.R., Rücker E.
Tetrahedron Letters , 1980
208.
α-Glykosidische Verknüpfung von D-Ribofuranose
Schmidt R.R., Hermentin P.
Angewandte Chemie , 1977
209.
A novel method for stereoselective glucuronidation
Fischer B., Nudelman A., Ruse M., Herzig J., Gottlieb H.E., Keinan E.
Journal of Organic Chemistry , 1984
211.
Stereospecific glycosylation by 1,2-O-cyanoethylidene derivatives of uronic acids
Betaneli V.I., Litvak M.M., Backinowsky L.V., Kochetkov N.K.
Carbohydrate Research , 1981
212.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) , 1966
214.
215
N. D. Tomashov
Zh. Prikl. Khim. , 1970
215.
Studies on glycosylation. II. A S-glycosylation by use of stannic chloride.
HONMA K., HAMADA A.
Chemical and Pharmaceutical Bulletin , 2011
216.
217
1925
217.
218.
α-D-Glucuronides of 1-(N-Alkyl-N-nitrosoamino)alkyl Alcohols
Braun H., Wiessler M.
Angewandte Chemie - International Edition , 1980
219.
Nucleosides. 114. 5'-O-Glucuronides of 5-fluorouridine and 5-fluorocytidine. Masked precursors of anticancer nucleosides
Watanabe K.A., Matsuda A., Halat M.J., Hollenberg D.H., Nisselbaum J.S., Fox J.J.
Journal of Medicinal Chemistry , 1981
220.
221
1960
221.
Dalgaard L., Svorstøl I., Høiland H., Songstad J.
Acta Chemica Scandinavica , 1983