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Chemical diversification of sialic acid glycosides by stereospecific, chemoselective deamination.

ABSTRACT: Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late-stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort.

SUBMITTER: Navuluri C

PROVIDER: S-EPMC3865865 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Chemical diversification of sialic acid glycosides by stereospecific, chemoselective deamination.

Navuluri Chandrasekhar C Crich David D

Angewandte Chemie (International ed. in English) 20130913 43

Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late-stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort. ...[more]

PMID: 24038615

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