Synthesis of D-erythro-sphingosine and D-erythro-ceramide

被引：36
|
作者：
Milne, JE
Jarowicki, K
Kocienski, PJ [1 ]
Alonso, J
机构：
[1] Univ Leeds, Dept Chem, Leeds LS2 9JT, W Yorkshire, England
[2] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33071 Oviedo, Spain
来源：
CHEMICAL COMMUNICATIONS | 2002年 / 05期
关键词：
D O I：
10.1039/b111071n
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A 1,2-metallate rearrangment of a higher order cuprate derived from an alpha-lithiated xylal derivative and tridecyllithium is the key step in a synthesis of D-erythro-sphingosine and ceramide. A convenient method for preparing alpha-lithiated glycals from alpha-phenylsulfinyl glycals is also described.
引用
收藏
页码：426 / 427
页数：2
相关论文
共 50 条
  • [1] ENANTIOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE AND OF CERAMIDE
    JULINA, R
    HERZIG, T
    BERNET, B
    VASELLA, A
    HELVETICA CHIMICA ACTA, 1986, 69 (02) : 368 - 373
  • [2] ENANTIOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE
    BERNET, B
    VASELLA, A
    TETRAHEDRON LETTERS, 1983, 24 (49) : 5491 - 5494
  • [3] Diastereoselective synthesis of D-erythro-sphingosine
    Spanu, P
    Rassu, G
    Pinna, L
    Battistini, L
    Casiraghi, G
    TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3237 - 3243
  • [4] STEREOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE
    NEWMAN, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (12) : 4098 - 4099
  • [5] AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF D-ERYTHRO-SPHINGOSINE
    RADUNZ, HE
    DEVANT, RM
    EIERMANN, V
    LIEBIGS ANNALEN DER CHEMIE, 1988, (11): : 1103 - 1105
  • [6] Synthesis of D-erythro-sphingosine from D-glucosamine
    Shinozaki, K
    Mizuno, K
    Masaki, Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (05) : 927 - 932
  • [7] Synthesis of D-erythro-sphingosine and D-erythro-sphinganine via 3-ketosphinganine
    Hoffman, RV
    Tao, JH
    TETRAHEDRON LETTERS, 1998, 39 (23) : 3953 - 3956
  • [8] A diversity oriented synthesis of D-erythro-sphingosine and siblings
    Ghosh, Amrita
    Chattopadhyay, Shital K.
    TETRAHEDRON-ASYMMETRY, 2017, 28 (09) : 1139 - 1143
  • [9] Synthesis of D-erythro-Sphingosine and D-erythro-Sphinganine Via 3-Ketosphinganine
    Hoffman, R. V.
    Tao, J.
    Tetrahedron Letters, 39 (23):
  • [10] Synthesis of D-erythro-Sphingosine from D-ribo-Phytosphingosine
    Ha, Hyun-Joon
    Yoon, Doo-Han
    Kang, Lae-Sung
    Hong, Myeng Chan
    Lee, Won Koo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (03): : 535 - 536
12345