Total synthesis of α-1 C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis

Journal of Organic Chemistry

Volumn 76, Issue 21, 2011, Pages 8588-8598

  Liu, Zheng ^a   Byun, Hoe Sup ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC EPOXIDATION; CYTOKINES; IN-VITRO; INVERSION OF CONFIGURATION; NATURAL KILLER CELLS; OLEFIN CROSS-METATHESIS; PHYTOSPHINGOSINES; SYNTHETIC ROUTES; TOTAL SYNTHESIS;

AMIDES; OLEFINS; STEREOCHEMISTRY; SUGARS;

SYNTHESIS (CHEMICAL);

1 O (ALPHA GALACTOPYRANOSYL) 2 HEXACOSANOYLAMINO 1,3,4 OCTADECANETRIOL; ALPHA 1C GALACTOSYLCERAMIDE; AMIDE; AMMONIUM CHLORIDE; CARBON; CYTOKINE; EPOXIDE; GALACTOSYLCERAMIDE; GLYCOSPHINGOLIPID; PHYTOSPHINGOSINE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; HUMAN; HUMAN CELL; RING OPENING METATHESIS POLYMERIZATION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; SYNTHESIS; TOTAL SYNTHESIS;

ADJUVANTS, IMMUNOLOGIC; ALKENES; EPOXY COMPOUNDS; GALACTOSYLCERAMIDES; GLYCOSPHINGOLIPIDS; HUMANS; IMMUNIZATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NATURAL KILLER T-CELLS; STEREOISOMERISM;

EID: 80055100954     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201450s     Document Type: Article

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