A convenient synthesis of S-glycosyl donors of sialic acid and their use for O-glycosylation

Sialic acid S-glycosyl donors were prepared efficiently in one step by use of S,S′-bis(1-phenyl-1 H-tetrazol-5-yl) dithiocarbonate ( 2) and used for O-glycosylation. The reaction of 2 with methyl 5-acetamido-4,7,8,9-tetra- O-acetyl-3,5-dideoxy- d- glycero-β- d- galacto-2-nonulopyranosonate gave meth...

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Bibliographic Details
Published in:Carbohydrate research 1990-08, Vol.203 (1), p.57-63
Main Authors: Takeda, Kazuyoshi, Tsuboyama, Kanoko, Torii, Katsumi, Furuhata, Kimio, Sato, Noriko, Ogura, Haruo
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Sialic acid S-glycosyl donors were prepared efficiently in one step by use of S,S′-bis(1-phenyl-1 H-tetrazol-5-yl) dithiocarbonate ( 2) and used for O-glycosylation. The reaction of 2 with methyl 5-acetamido-4,7,8,9-tetra- O-acetyl-3,5-dideoxy- d- glycero-β- d- galacto-2-nonulopyranosonate gave methyl [1-phenyl-1 H-tetrazol-5-yl 5-acetamido-4,7,8,9-tetra- O-acetyl-3,5-dideoxy-2-thio- d- glycero- a- ( 4) and -β- d- galacto-2-nonulopyranosid]onate ( 5), and 1-phenyl-1 H-tetrazol-5-yl (methyl 5-acetamido-4,7,8,9-tetra- O-acetyl-3,5-dideoxy- d- glycero- d- galacto-2-nonulopyranoside)thionate. Compounds 4 and 5 could be applied to the synthesis of a sialosyl-(2→6′)-lactose derivative and cholester-3-yl sialoside, respectively.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)80045-5