The Journal of organic chemistry

Asymmetric synthesis of d-ribo-phytosphingosine from 1-tetradecyne and (4-methoxyphenoxy) acetaldehyde

Z Liu, HS Byun, R Bittman

Index: Liu, Zheng; Byun, Hoe-Sup; Bittman, Robert Journal of Organic Chemistry, 2010 , vol. 75, # 13 p. 4356 - 4364

Full Text: HTML

Citation Number: 21

Abstract

An asymmetric synthesis of d-ribo-phytosphingosine (1) was achieved by utilizing the ProPhenol (12)-catalyzed alkynylation of unsaturated aldehyde 8 to afford allylic propargylic alcohol (S)-6 followed by asymmetric epoxidation and opening of propargylic epoxy alcohol anti-5 with NaN3/NH4Cl. Deprotection and reduction of the resulting acyclic azide 3 then gave 1. Alkyne− azide 3 was subjected to an intramolecular click reaction, generating a ...

Related Articles:

Stereochemistry associated with the addition of 2-(trimethylsilyl) thiazole to differentially protected. alpha.-amino aldehydes. Applications toward the synthesis of …

[Dondoni, Alessandro; Fantin, Giancarlo; Fogagnolo, Marco; Pedrini, Paola Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1439 - 1446]

A common and stereoselective strategy for the synthesis of N, O, O, O-tetra-acetyl D-ribo-(2S, 3S, 4R)-phytosphingosine and 2-epi-jaspine B

[Tetrahedron Letters, , vol. 52, # 38 p. 4861 - 4864]

Phytoceramides and acylated phytosterol glucosides from Pterospermum acerifolium Willd. seed coat and their osteogenic activity

[Phytochemistry, , vol. 81, p. 117 - 125]

A concise route to phytosphingosine from lyxose

[Lin, Chun-Cheng; Fan, Gang-Ting; Fang, Jim-Min Tetrahedron Letters, 2003 , vol. 44, # 28 p. 5281 - 5283]

Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

[Tsujimoto, Takashi; Ito, Yukishige Tetrahedron Letters, 2007 , vol. 48, # 31 p. 5513 - 5516]

More Articles...