Journal ArticleDOI
The chloroacetyl group in synthetic carbohydrate chemistry
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TLDR
A number of O -chloroacetyl derivatives of d -glucose have been prepared as mentioned in this paper, and they can be removed with facility by treatment with thiourea to yield the parent carbohydrate derivative, they serve as valuable tools in synthetic carbohydrate chemistry.About:
This article is published in Carbohydrate Research.The article was published on 1970-11-01. It has received 106 citations till now. The article focuses on the topics: Carbohydrate chemistry.read more
Citations
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Book ChapterDOI
The Selective Removal of Protecting Groups in Carrohydrate Chemistry
TL;DR: In this article, the selective introduction of substituents into carbohydrates and the hydrolysis, acetolysis, and isomerization of polyacetals is discussed, and it is shown that the acid-catalyzed isomerisation of carbohydrate acetals occurs with favored cleavage of only one of the two acetal carbon-to-oxygen bonds.
Journal ArticleDOI
Synthesis of heparin fragments. A chemical synthesis of the trisaccharide O-(2-deoxy-2-sulfamido-3,6-di-O-sulfo-α-d-glucopyranosyl)-(1→4)-O-(2-O-sulfo-α-l-idopyranosyluronic acid)-(1→4)-2-deoxy-2-sulfamido-6-O-sulfo-d-glucopyranose heptasodium salt
Jean-Claude Jacquinet,Maurice Petitou,Philippe Duchaussoy,Isidore Lederman,Jean Choay,Giangiacomo Torri,Pierre Sinaÿ +6 more
TL;DR: In this article, a fragment of the minimal antithbin III binding region in heparin, neither of which binds to antithXbin III nor binds to AntithXin III nor binding to Antisaccharide, was converted into methyl 4-O -acetyl-3- O -benzylβ- l -idopyranuronate 1,2-( tert -butyl orthoacetate).
Journal ArticleDOI
Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei.
Chikara Murakata,Tomoya Ogawa +1 more
TL;DR: The total synthesis of the GPI anchor of Trypanosoma brucei was achieved for the first time and the introduction of two phosphodiester functions was efficiently achieved using the H-phosphonate method.
Book ChapterDOI
Cyclic Acetals of The Aldoses and Aldosides Highlights of the Literature Since 1964, and A Supplement to the Tables
TL;DR: The formation of cyclic acetals occurs by condensation of a diol with an aldehyde or ketone, the carbonyl compound often serving as the solvent.
Journal ArticleDOI
Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1.
TL;DR: Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
References
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Journal ArticleDOI
Stevioside. i. the structure of the glucose moieties
Journal ArticleDOI
I-(Indole-3-acetyl)-β- D -Glucose, a New Compound in the Metabolism of Indole-3-acetic Acid in Plants
TL;DR: A trace amount of a compound which showed definitely indole reactive properties and which was split on alkaline hydrolysis into IAA was observed, besides indoleacetylaspartic acid1 (IAAsp), which was found in the leaves of the monocotyledonous plant Colchicum neapolitanum Ten.
Journal ArticleDOI
Oxidative demethylation with chromium trioxide in acetic acid
Stephen J. Angyal,K. James +1 more
Journal ArticleDOI
Syntheses with Partially Benzylated Sugars. II.1 The Anomeric 1-O-Benzoyl-L-arabinopyranoses and 1-O-Benzoyl-L-arabinofuranoses and Their Tendencies to Undergo Acyl Migration
Journal ArticleDOI
A comparison of the properties of pentaacetates and methyl 1,2-orthoacetates of glucose and mannose
R. U. Lemieux,Carol Brice +1 more
TL;DR: The rates of exchange of acetate, concurrent with anomerization, between the C1-acetoxy groups of the pentaacetates (0.05 m) of D-glucose and D-mannose and stannic trichloride acetate ( 0.05m) in chl...