Highly diastereoselective synthesis of two analogues of dihydrosphingosine

被引：33
|
作者：
Villard, R [1 ]
Fotiadu, F [1 ]
Buono, G [1 ]
机构：
[1] Ecole Natl Super Synth Proc & Ingn Chim Aix Marse, UMR 6516, F-13397 Marseille 20, France
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 04期
关键词：
D O I：
10.1016/S0957-4166(98)00030-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Diastereomeric analogues 8 and 9 of dihydrosphingosine 2 with a shortened alkyl chain were obtained with high diastereoselectivity via addition of n-hexyl magnesium bromide or dihexylzinc to a chiral aldehyde 3, respectively. These compounds are precursors of new potentially hydrosoluble analogues of glycosphingolipides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：607 / 611
页数：5
相关论文
共 50 条
  • [21] Enantiospecific, diastereoselective synthesis of Aspidosperma alkaloid analogues from secolaganin
    Brown, RT
    Kandasamy, M
    TETRAHEDRON LETTERS, 2000, 41 (19) : 3547 - 3550
  • [22] A highly diastereoselective total synthesis of (±)-heritonin and (±)-heritol
    Chavan, Subhash P.
    Garai, Sumanta
    Kalkote, Uttam R.
    TETRAHEDRON, 2012, 68 (40) : 8509 - 8514
  • [23] A highly diastereoselective synthesis of the southwestern quadrant of micoticin A
    Mortensen, Matthew S.
    O'Doherty, George A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3433 - U3434
  • [24] Highly diastereoselective synthesis of a novel functionalized triepoxytrinaphthylene
    Erdogan, Musa
    Essiz, Selcuk
    Fabris, Fabrizio
    Dastan, Arif
    ARKIVOC, 2018, : 134 - 143
  • [25] Highly diastereoselective synthesis of chimeras of proline and glutamate
    Kudryavtsev, Konstantin V.
    Tsentalovich, Mikhail Yu.
    Yegorov, Anton S.
    Kolychev, Eugene L.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) : 1461 - 1466
  • [26] Diastereoselective Synthesis of Highly Functionalized Proline Derivatives
    Philippova, Anna N.
    Vorobyeva, Daria V.
    Gribanov, Pavel S.
    Dolgushin, Fedor M.
    Osipov, Sergey N.
    MOLECULES, 2022, 27 (20):
  • [27] Diastereoselective Synthesis and Diversification of Highly Functionalized Cyclopentanones
    Baumann, Marcus
    Baxendale, Ian R.
    SYNTHESIS-STUTTGART, 2018, 50 (04): : 753 - 759
  • [28] Highly diastereoselective synthesis of pederic acid derivatives
    Roush, WR
    Marron, TG
    Pfeifer, LA
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (03): : 474 - 478
  • [29] Diastereoselective synthesis of ω-phosphonic acid analogues of 4-arylkainoids
    Yuasa, Y
    Fujimaki, N
    Yokomatsu, T
    Ando, J
    Shibuya, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (21): : 3577 - 3584
  • [30] Regioselective and diastereoselective synthesis of highly substituted cyclopentanes
    Hubbard, RD
    Miller, BL
    TETRAHEDRON, 2003, 59 (41) : 8143 - 8152
12345