A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

被引:44
作者
Cai, Y [1 ]
Ling, CC [1 ]
Bundle, DR [1 ]
机构
[1] Univ Alberta, Dept Chem, Alberta Ingenu Ctr Carbohydrate Sci, Edmonton, AB T6G 2G2, Canada
关键词
D O I
10.1039/b516333a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.
引用
收藏
页码:1140 / 1146
页数:7
相关论文
共 75 条
[1]   A new diorganozinc-based enantioselective access to truncated D-ribo-phytosphingosine [J].
Ayad, T ;
Génisson, Y ;
Verdu, A ;
Baltas, M ;
Gorrichon, L .
TETRAHEDRON LETTERS, 2003, 44 (03) :579-582
[2]   Stereospecific total syntheses of sphingosine and its analogues from L-serine [J].
Azuma, H ;
Tamagaki, S ;
Ogino, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3538-3541
[3]   Thiooligosaccharide conjugate vaccines evoke antibodies specific for native antigens [J].
Bundle, DR ;
Rich, JR ;
Jacques, S ;
Yu, HN ;
Nitz, M ;
Ling, CC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7725-7729
[4]  
BUNDLE DR, 2003, Patent No. 03101937
[5]   Glycolipids from sponges.: 6.: Plakoside A and B, two unique prenylated glycosphingolipids with immunosuppressive activity from the marine sponge Plakortis simplex [J].
Costantino, V ;
Fattorusso, E ;
Mangoni, A ;
Di Rosa, M ;
Ianaro, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (51) :12465-12470
[6]  
Curfman C, 2000, METHOD ENZYMOL, V311, P391
[7]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[8]   Sphingolipids are potential heat stress signals in Saccharomyces [J].
Dickson, RC ;
Nagiec, EE ;
Skrzypek, M ;
Tillman, P ;
Wells, GB ;
Lester, RL .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (48) :30196-30200
[9]   STEREOCHEMISTRY ASSOCIATED WITH THE ADDITION OF 2-(TRIMETHYLSILYL)THIAZOLE TO DIFFERENTIALLY PROTECTED ALPHA-AMINO ALDEHYDES - APPLICATIONS TOWARD THE SYNTHESIS OF AMINO-SUGARS AND SPHINGOSINES [J].
DONDONI, A ;
FANTIN, G ;
FOGAGNOLO, M ;
PEDRINI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1439-1446
[10]   Double stereodifferentiation in asymmetric dihydroxylation:: application to the first diastereoselective synthesis of L-xylo-[2R,3S,4S]-C18-phytosphingosine [J].
Fernandes, RA ;
Kumar, P .
TETRAHEDRON LETTERS, 2000, 41 (52) :10309-10312