- Efficient and versatile synthesis of (2S,3R)-sphingosine and its 2-azido-3-O-benzylsphingosine analogue
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The title compounds (1, 2) were synthesized from (2R,3S)-2-O-benzyl-3,4-O- (3′-pentylidene)-2,3,4-trihydroxybutanal (5). Installation of the E-double bond and aliphatic chain into the sphingosine base was effected by a sequence of Horner-Wadsworth-Emmons olefination of 5, conversion to allylic acetate 8, and copper-mediated Grignard coupling. The method is versatile, allowing a broad variety of aliphatic chains to be introduced in the organocuprate coupling step.
- Lu, Xuequan,Bittman, Robert
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p. 1873 - 1875
(2007/10/03)
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- 'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
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A stereocontrolled synthesis of globotriaosylceramide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting 'armed-disarmed' glycosidation methodology based on glycosyl donors and acceptors carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl(1→4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient.
- Hashimoto, Shun-Ichi,Sakamoto, Hiroki,Honda, Takeshi,Abe, Hiroshi,Nakamura, Sei-Ichi,Ikegami, Shiro
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p. 8969 - 8972
(2007/10/03)
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