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

Wipf, P and Pierce, JG (2006) Expedient synthesis of the α-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000). Organic Letters, 8 (15). 3375 - 3378. ISSN 1523-7060

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Abstract

Key reactions in a concise synthesis of an α-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. © 2006 American Chemical Society.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Pierce, JG
Date: 20 July 2006
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 8
Number: 15
Page Range: 3375 - 3378
DOI or Unique Handle: 10.1021/ol0613057
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Adjuvants, Immunologic--chemical synthesis; Adjuvants, Immunologic--pharmacology; Galactosylceramides--chemical synthesis; Galactosylceramides--pharmacology; Glycosides--chemical synthesis; Imines--chemistry; Molecular Structure; Stereoisomerism
PubMed ID: 16836409
Date Deposited: 30 Oct 2013 16:57
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/19897

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