Journal ArticleDOI
Selective preparation of glycosyl sulfone or glycal by treatment of phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid
TLDR
Treatment of acetylated phenyl thioglycoside of N-acetylneuraminic acid with MCPBA in CH2Cl2 affords quantitatively mixtures of the respective sulfone and glycal free from the sulfoxide that can be regarded as a new method for the preparation of sialic acid glycals.Abstract:
Treatment of acetylated phenyl thioglycoside of N-acetylneuraminic acid with m-chloroperbenzoic acid (MCPBA) in CH2Cl2 affords quantitatively mixtures of the respective sulfone and glycal free from the sulfoxide. The outcome of the reaction does not depend on the anomeric configuration of the starting thioglycoside. The sulfone can be selectively prepared (yield ∼100%) by oxidation with an excess of MCPBA and NaHCO3. In the presence of pyridine (2 equiv.) and MCPBA (2 equiv.), the major product is glycal (yields 81—88%). This version of the reaction can be regarded as a new method for the preparation of sialic acid glycals.read more
Citations
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Journal ArticleDOI
Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers.
TL;DR: Six compounds, including three new decarboxylated sialic acid dimers, were also found to have been synthesized in the reaction, and all of the side products were isolated and fully characterized.
Book ChapterDOI
Chemical Synthesis of Glycosides of N-Acetylneuraminic Acid.
Cristina De Meo,Bradley T Jones +1 more
TL;DR: This review presents major accomplishments in the field of stereoselective synthesis of sialosides, with the emphasis on significant breakthroughs and influential synthetic strategies of the last decade.
Journal ArticleDOI
Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis.
TL;DR: Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.
Journal ArticleDOI
One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid
TL;DR: A facile and highly efficient microwave-assisted preparation of Neu5Ac1Me using silica sulfuric acid (SSA) as solid-supported acid catalyst that is one- to two-orders of magnitude faster than standard procedures is reported.
Journal ArticleDOI
Selective Preparation of Glycosyl Sulfone or Glycal by Treatment of Phenyl Thioglycoside of N‐Acetylneuraminic Acid with m‐Chloroperbenzoic Acid.
TL;DR: In this paper, N-acetylneuraminic acid was treated with m-chloroperbenzoic acid (MCPBA) in CH2Cl2 to obtain mixtures of the respective sulfone and glycal free from the sulfoxide.
References
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Journal ArticleDOI
Recent progress in O-glycosylation methods and its application to natural products synthesis
Kazunobu Toshima,Kuniaki Tatsuta +1 more
Reference BookDOI
Preparative carbohydrate chemistry
TL;DR: The authors discusses the reactions and derivative forms of carbohydrates and discusses commonly used methods and procedures, and illustrates bond-forming reactions of SN2 types, free radicals, chain extensions, and branching.
Journal ArticleDOI
Glycosylation of unreactive substrates
TL;DR: Synthese de glucosteroide et d'arylglucoside a partir d'ethoxycarbonyloxy-3 hydroxy-7 cholanoate-24 acide et de phenyl tetra-O-benzyl-2,3,4,6 glucopyranosyl sulfoxyde