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Synthesis of C-glycoside analogues of ?-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

ABSTRACT: C-Glycoside analogues of ?-galactosylceramide were synthesized in which several significant modifications known to promote Th-1 cytokine production were included. The key transformations include C-H oxidation, Sharpless asymmetric epoxidation, olefin cross metathesis, and an allyl cyanate to isocyanate rearrangement.

SUBMITTER: Liu Z

PROVIDER: S-EPMC3263403 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

Liu Zheng Z Bittman Robert R

Organic letters 20120110 2

C-Glycoside analogues of α-galactosylceramide were synthesized in which several significant modifications known to promote Th-1 cytokine production were included. The key transformations include C-H oxidation, Sharpless asymmetric epoxidation, olefin cross metathesis, and an allyl cyanate to isocyanate rearrangement. ...[more]

PMID: 22233351

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