Synthesis of N-Glycoly1-8-O-sulfoneuraminic Acid

Makoto Tanaka; Toshitsugu Kai; Xue Sun; Hiroaki Takayanagi; Kimio Furuhata

doi:10.1248/cpb.43.2095

Synthesis of N-Glycoly1-8-O-sulfoneuraminic Acid

Makoto Tanaka
, Toshitsugu Kai
, Xue Sun
, Hiroaki Takayanagi
, Kimio Furuhata

Chemistry

Kitasato University

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neuraminic acid O-benzyl α-glycoside (3) and neuraminic acid S-methyl α-glucoside (10) were prepared from readily available N-acetylneuraminic acid. The structures of these compounds were confirmed by analysis of their NMR spectra. © 1995, The Pharmaceutical Society of Japan. All rights reserved.

Original language	English
Pages (from-to)	2095-2098
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	43
Issue number	12
DOIs	https://doi.org/10.1248/cpb.43.2095
State	Published - Jan 1 1995

Keywords

N-glycolyl-8-O-sulfoneuraminic acid
sa-ponification
sialic acid
sulfation
sulfur trioxide trimethylamine complex

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10.1248/cpb.43.2095

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abstract = "N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neuraminic acid O-benzyl α-glycoside (3) and neuraminic acid S-methyl α-glucoside (10) were prepared from readily available N-acetylneuraminic acid. The structures of these compounds were confirmed by analysis of their NMR spectra. {\textcopyright} 1995, The Pharmaceutical Society of Japan. All rights reserved.",

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AU - Tanaka, Makoto

AU - Kai, Toshitsugu

AU - Sun, Xue

AU - Takayanagi, Hiroaki

AU - Furuhata, Kimio

PY - 1995/1/1

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N2 - N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neuraminic acid O-benzyl α-glycoside (3) and neuraminic acid S-methyl α-glucoside (10) were prepared from readily available N-acetylneuraminic acid. The structures of these compounds were confirmed by analysis of their NMR spectra. © 1995, The Pharmaceutical Society of Japan. All rights reserved.

AB - N-Glycolyl-8-O-sulfoneuraminic acid (1) was synthesized for the first time in good yield. The key intermediates for synthesis of 1, neuraminic acid O-benzyl α-glycoside (3) and neuraminic acid S-methyl α-glucoside (10) were prepared from readily available N-acetylneuraminic acid. The structures of these compounds were confirmed by analysis of their NMR spectra. © 1995, The Pharmaceutical Society of Japan. All rights reserved.

KW - N-glycolyl-8-O-sulfoneuraminic acid

KW - sa-ponification

KW - sialic acid

KW - sulfation

KW - sulfur trioxide trimethylamine complex

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EP - 2098

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

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Synthesis of N-Glycoly1-8-O-sulfoneuraminic Acid

Abstract

Keywords

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