Improved synthesis of phytosphingosine and dihydrosphingosine from 3,4,6-tri-O-benzyl-D-galactal

被引:12
作者
Niu, Youhong [2 ]
Cao, Xiaoping [2 ]
Ye, Xin-Shan [1 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
D O I
10.1002/hlca.200890076
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and facile synthesis of phytosphingosine and dihydrosphingosine derivatives is described with less steps and in improved overall yield (66-72%) starting from commercially available tri-O-benzyl-D-galactal. The key steps include Wittig reaction, Mitsunobu transformation, reduction, and deprotection.
引用
收藏
页码:746 / 752
页数:7
相关论文
共 42 条
[11]   Natural killer-like nonspecific tumor cell lysis mediated by specific ligand-activated Vα14 NKT cells [J].
Kawano, T ;
Cui, JQ ;
Koezuka, Y ;
Toura, I ;
Kaneko, Y ;
Sato, H ;
Kondo, E ;
Harada, M ;
Koseki, H ;
Nakayama, T ;
Tanaka, Y ;
Taniguchi, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (10) :5690-5693
[12]   CD1d-restricted and TCR-mediated activation of V(alpha)14 NKT cells by glycosylceramides [J].
Kawano, T ;
Cui, JQ ;
Koezuka, Y ;
Toura, I ;
Kaneko, Y ;
Motoki, K ;
Ueno, H ;
Nakagawa, R ;
Sato, H ;
Kondo, E ;
Koseki, H ;
Taniguchi, M .
SCIENCE, 1997, 278 (5343) :1626-1629
[13]  
Kolter T, 1999, ANGEW CHEM INT EDIT, V38, P1532, DOI 10.1002/(SICI)1521-3773(19990601)38:11<1532::AID-ANIE1532>3.0.CO
[14]  
2-U
[15]   A concise route to phytosphingosine from lyxose [J].
Lin, CC ;
Fan, GT ;
Fang, JM .
TETRAHEDRON LETTERS, 2003, 44 (28) :5281-5283
[16]   An efficient high-yield synthesis of D-ribo-phytosphingosine [J].
Lombardo, Marco ;
Guiteras Capdevila, Montse ;
Pasi, Filippo ;
Trombini, Claudio .
ORGANIC LETTERS, 2006, 8 (15) :3303-3305
[17]   Synthesis of D-ribo-C18-phytosphingosine from D-glucosamine via the D-allosamine derivatives as key intermediates [J].
Luo, SY ;
Thopate, SR ;
Hsu, CY ;
Hung, SC .
TETRAHEDRON LETTERS, 2002, 43 (27) :4889-4892
[18]  
MAURER BJ, 2000, AACR ANN M ABSTR, P1520
[19]  
MIYSUNOBU O, 1981, SYNTHESIS-STUTTGART, P1
[20]  
MORI K, 1994, LIEBIGS ANN CHEM, P41