Journal ArticleDOI
Highly stereoselective glycosylation of N-acetylneuraminic acid aided by a phenylthio substituent as a stereocontrolling auxilliary
Yukishige Ito,Tomoya Ogawa +1 more
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TLDR
The 2-halo-3β-phenylthio derivatives of N-acetylneuraminic acid afforded 2α-glycosides in a high stereoselectivity as mentioned in this paper.About:
This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 71 citations till now. The article focuses on the topics: Substituent & Stereoselectivity.read more
Citations
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Journal ArticleDOI
Toward automated oligosaccharide synthesis.
TL;DR: The methods developed to tackle the problems of carbohydrate-mediated biological processes are described, with particular focus on the issue related to the development of the automated synthesis of oligosaccharides.
Book ChapterDOI
Chapter 11 – Chemistry, biochemistry and biology of sialic acids ☆
Journal ArticleDOI
Glycosidation of sialic acid
Kaoru Okamoto,Toshio Goto +1 more
TL;DR: Enzymic and synthetic approaches to the glycosidation of sialic acid by new methodologies are discussed, which aim to clarify their vital functions and identify the most difficult problem remaining.
Journal ArticleDOI
Highly Alpha‐Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
Che-Hsiung Hsu,Kuo-Ching Chu,Yih-Shyan Lin,Jeng-Liang Han,Yu-Shiang Peng,Chien-Tai Ren,Chung-Yi Wu,Chi-Huey Wong,Chi-Huey Wong +8 more
TL;DR: A new sialylation reagent 1 is reported that employs an N-acetyl-5-N,4-O-carbonyl protection with dibutyl phosphate as the leaving group and the new donor was applied to develop efficient strategies to use to create natural sialosides.
Book ChapterDOI
Chemistry and Developments of Fluorinated Carbohydrates
TL;DR: This chapter presents a review about the chemistry and developments of fluorinated carbohydrates, a review of natural nucleoside analogs having effective antiviral and antitumor activities with low cytotoxicity for the host cells.
References
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Journal ArticleDOI
The use of 1-O-tosyl-d-glucopyranose derivatives in α-d-glucoside synthesis
Ronald Eby,Conrad Schuerch +1 more
TL;DR: The 1-O-tosyl-d-glucopyranose derivatives have been shown to react rapidly in various solvents with low concentrations of alcohols, either methanol or methyl 2,3,4-tri-O-,tri-n-Obenzyl-α-d -glucophosphamide derivatives.
Journal ArticleDOI
Functionalization of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid methyl ester.
TL;DR: In this article, the acetyl protected 2-deoxy-2,3-dehydroneuraminic acid methyl ester was functionalized by modifying its 2-3-double bond to convert it into new glycosyl donors such as 2, 3-dibromo-, 2.3-epoxy-, and 2-halo-3,hydroxyneuraminaic acid derivatives.
Journal ArticleDOI
An efficient approach to streoselective glycosylation of N-acetylneuraminic acid: Used of phenylselenyl group as a stereocontrolling auxillary
Yukishige Ito,Tomoya Ogawa +1 more
TL;DR: In this article, selective glycosylation of N-acetylneuraminic acid was achieved by use of the fluoride 3 which carries 3β-phenylselenyl substituent.
Journal ArticleDOI
Glycosidsynthese von N-acetylneuraminsäure mit sekundären Hydroxylgruppen
Hans Paulsen,Ulrich von Deessen +1 more
Journal ArticleDOI
An effective synthesis of α-glycosides of N-acetylneuraminic acid derivatives by use of 2-deoxy-2β-halo-3β-hydroxy-4,7,8,9-tetra-O-acetyl- N-acetylneuraminic acid methyl ester
TL;DR: In this paper, the acetyl protected 2-deoxy-2β-halo-3β-hydroxy- N -acetylneuraminic acid methyl ester with various acceptors such as properly protected glucose, galactose, and lactose derivatives in the presence of silver triflate gave the NauAc α-glycosides in preference to the corresponding α- glycosides.