An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate:: a short synthesis of D-myo-inositol-4-phosphate

被引：15
|
作者：
Sureshan, KM [1 ]
Watanabe, Y [1 ]
机构：
[1] Ehime Univ, Dept Appl Chem, Fac Engn, Matsuyama, Ehime 7908577, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 07期
基金：
日本学术振兴会;
关键词：
D O I：
10.1016/j.tetasy.2004.02.020
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both the diastereomers could be separated by column chromatography. The absolute configurations of the diastereomers were determined by converting the less polar diastereomer to the known L-2,4-di-O-benzyl-myo-inositol. The utility of the resolved derivatives is illustrated by a short and efficient synthesis of D-myo-inositol-4-phosphate in four steps from myo-inositol. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1193 / 1198
页数：6
相关论文
共 50 条
  • [21] Efficient syntheses of optically pure chiro- and allo-inositol derivatives, azidocyclitols and aminocyclitols from myo-inositol
    Sureshan, Kana M.
    Ikeda, Kyoko
    Asano, Naoki
    Watanabe, Yutaka
    TETRAHEDRON, 2008, 64 (18) : 4072 - 4080
  • [22] AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE D-MYO-INOSITOL 1,4,5-TRIPHOSPHATE
    LIU, YC
    CHEN, CS
    TETRAHEDRON LETTERS, 1989, 30 (13) : 1617 - 1620
  • [23] Sulfonate protecting groups.: Regioselective sulfonylation of myo-inositol orthoesters -: improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives
    Sureshan, KM
    Shashidhar, MS
    Praveen, T
    Gonnade, RG
    Bhadbhade, MM
    CARBOHYDRATE RESEARCH, 2002, 337 (24) : 2399 - 2410
  • [24] Achieving molecular stability of racemic 4-O-benzyl-myo-inositol-1,3,5-orthoformate through crystal formation
    Sardessai, Richa
    Krishnaswamy, Shobhana
    Shashidhar, Mysore S.
    CRYSTENGCOMM, 2012, 14 (23): : 8010 - 8016
  • [25] General synthesis of 3-phosphorylated myo-inositol phospholipids and derivatives
    Painter, GF
    Grove, SJA
    Gilbert, IH
    Holmes, AB
    Raithby, PR
    Hill, ML
    Hawkins, PT
    Stephens, LR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08): : 923 - 935
  • [26] SYNTHESIS OF 1-PHOSPHATIDYL-MYO-INOSITOL-4-PHOSPHATE
    KOZLOVA, SP
    TARUSOVA, NB
    PREOBRAZ.NA
    JOURNAL OF GENERAL CHEMISTRY USSR, 1969, 39 (11): : 2403 - &
  • [27] myo-Inositol 1,4,6-trisphosphorothioate and myo-inositol 1,3,6-trisphosphorothioate:: partial agonists with very low intrinsic activity at the platelet myo-inositol 1,4,5-trisphosphate receptor
    Murphy, CT
    Riley, AM
    Mills, SJ
    Lindley, CJ
    Potter, BVL
    Westwick, J
    MOLECULAR PHARMACOLOGY, 2000, 57 (03) : 595 - 601
  • [28] Synthesis of caged myo-inositol 1,3,4,5-tetrakisphosphate
    Dinkel, C
    Schultz, C
    TETRAHEDRON LETTERS, 2003, 44 (06) : 1157 - 1159
  • [29] SYNTHESIS OF (+/-)-MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND THE NOVEL ANALOG (+/-)-MYO-INOSITOL 1,4-BISPHOSPHATE 5-PHOSPHOROTHIOATE
    NOBLE, NJ
    COOKE, AM
    POTTER, BVL
    CARBOHYDRATE RESEARCH, 1992, 234 : 177 - 187
  • [30] TOTAL SYNTHESIS OF D-MYO-INOSITOL AND L-MYO-INOSITOL 1,4,5-TRISPHOSPHATE
    VACCA, JP
    DESOLMS, SJ
    HUFF, JR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) : 3478 - 3479
12345