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Literature DB >> 16836409

Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

Abstract

[Structure: see text] Key reactions in a concise synthesis of an alpha-C-galactosylceramide analogue of KRN7000 include a diastereoselective alkenylalane addition to an N-tert-butanesulfinyl imine and the use of an epoxidation/carbamate ring opening sequence to install the aminodiol stereotriad.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16836409 DOI： 10.1021/ol0613057

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

15 in total

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5. Large-scale asymmetric synthesis of the bioprotective agent JP4-039 and analogs.

Authors: Marie-Céline Frantz; Joshua G Pierce; Joan M Pierce; Li Kangying; Wan Qingwei; Matthew Johnson; Peter Wipf
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6. Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

Authors: Zheng Liu; Robert Bittman
Journal: Org Lett Date: 2012-01-10 Impact factor: 6.005

7. Synthesis of immunostimulatory alpha-C-galactosylceramide glycolipids via Sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening.

Authors: Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal: Org Lett Date: 2010-07-02 Impact factor: 6.005