Enantioselective Synthesis of Homosphingosine Derivatives from L-Aspartic Acid

被引：8

作者：

Sauerland, Sami J. K. ^{[1
]}

Castillo-Melendez, Joel A. ^{[1
]}

Nattinen, Kalle ^{[2
]}

Rissanen, Kari ^{[2
]}

Koskinen, Ari M. P. ^{[1
]}

机构：

[1] Aalto Univ, Organ Chem Lab, Dept Chem Technol, Helsinki 02015, Finland

[2] Univ Jyvaskyla, Dept Chem, Xray Crystallog Nanosci Ctr, SF-40100 Jyvaskyla, Finland

来源：

SYNTHESIS-STUTTGART | 2010年 / 05期

关键词：

diastereoselectivity; enantioselectivity; sphingosine; ceramide; AMINO; SPHINGOSINE; OLEFINATION; INHIBITION;

D O I：

10.1055/s-0029-1219081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The sterically demanding 9-phenylfluorenyl N-protection of a number of amino acids allows the formation of amino acid derived beta-ketophosphonate reagents and their Horner-Wadsworth-Emmons olefination. In an attempt to develop a synthesis of Derythro-homosphingosine in enantiopure form, we have shown that the reactivity of the intermediates is influenced by the distinctive conformational requirements of this large protecting group.

引用

页码：757 / 762

页数：6

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