Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol

Journal of Organic Chemistry

Volumn 70, Issue 6, 2005, Pages 2398-2401

  Murata, Kenji ^a   Toba, Tetsuya ^a   Nakanishi, Kyoko ^a   Takahashi, Bitoku ^a   Yamamura, Takashi ^b   Miyake, Sachiko ^b   Annoura, Hirokazu ^a  

^a SUNTORY LTD   (Japan)

^b NATIONAL INSTITUTE OF NEUROSCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; DISEASES; IMMUNOLOGY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

AUTOIMMUNE DISEASES; GLYCOLIPIDS; PHYTOSPHINGOLIPIDS; SPHINGOSINE;

LIPIDS;

1 O (ALPHA DEXTRO GALACTOSYL) 2 TETRACOSANOYLAMINO 1,3,4 NONANETRIOL; ARABINITOL; EPOXIDE; GLYCOLIPID; HALIDE; IMMUNOSUPPRESSIVE AGENT; SPHINGOSINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; AUTOIMMUNE DISEASE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; COMMERCIAL PHENOMENA; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GLYCOSIDATION; MASS SPECTROMETRY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY; TH1 CELL;

GLYCOSPHINGOLIPIDS; IMMUNOSUPPRESSIVE AGENTS; MOLECULAR CONFORMATION;

EID: 15444380934     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048151y     Document Type: Article

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37. Halide ion catalyzed glycosidation reaction was reported for the synthesis of α-linked disaccharide: (a) Spohr, U.; Le, N.; Ling, C.-C.; Lemieux, R. U. Can. J. Chem. 2001, 79, 238. (b) Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056. Similar glycosidation methodology although in lower yield was reported: (c) Vo-Hoang, Y.; Micouin, L.; Ronet, C.; Gachelin, G.; Bonin, M. ChemBioChem 2003, 4, 27.