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Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9.

ABSTRACT: A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield.

SUBMITTER: Santra A

PROVIDER: S-EPMC3182426 | biostudies-literature | 2011

REPOSITORIES: biostudies-literature

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Convergent synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9.

Santra Abhishek A Misra Anup Kumar AK

Beilstein journal of organic chemistry 20110829

A convenient synthesis of the tetrasaccharide repeating unit of the O-antigen of Shigella boydii type 9 has been achieved in excellent yield using a [2 + 2] block glycosylation strategy. TEMPO-mediated selective oxidation of the primary alcohol of the tetrasaccharide derivative 8 to the carboxylic group followed by deprotection of the functional groups furnished target tetrasaccharide 1 as its 4-methoxyphenyl glycoside in high yield. ...[more]

PMID: 21977201

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