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Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

ABSTRACT: It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in oligosaccharide synthesis.

SUBMITTER: Ranade SC

PROVIDER: S-EPMC3005820 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature

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Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

Ranade Sneha C SC Kaeothip Sophon S Demchenko Alexei V AV

Organic letters 20101118 24

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting gro ...[more]

PMID: 21087037

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Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

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Glycosyl alkoxythioimidates as complementary building blocks for chemical glycosylation.

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