A simple and practical resolution of 1,2:4,5-di-O-isopropylidene-myo-inositol

被引:21
作者
Sureshan, KM [1 ]
Yamasaki, T [1 ]
Hayashi, M [1 ]
Watanabe, Y [1 ]
机构
[1] Ehime Univ, Fac Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/S0957-4166(03)00402-6
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 1,2:4,5-di-O-isopropylidene-myo-inositol has been developed. The diketal was converted to diastereomeric 3,6-di-O-mandelates by the reaction with (S)-O-acetylmandeloyl chloride. Both the diastereomers could be separated by sequential crystallization in multi-gram quantities. The enantiomers of the diol were obtained by removal of the chiral auxiliaries. Also the trans-isopropylidene was cleaved efficiently to obtain another pair of chiral diols. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1771 / 1774
页数:4
相关论文
共 25 条
[1]   INOSITOL TRISPHOSPHATE AND CALCIUM SIGNALING [J].
BERRIDGE, MJ .
NATURE, 1993, 361 (6410) :315-325
[2]  
Bruzik K. S., 1999, ACS S SERIES, V718
[3]   Synthesis of acyclic and heterocyclic natural products utilizing cyclitols as novel chiral building blocks [J].
Chida, N ;
Ogawa, S .
CHEMICAL COMMUNICATIONS, 1997, (09) :807-813
[4]   Syntheses of D- and L-myo-inositol 1,2,4,5-tetrakisphosphate and stereoselectivity of the I(1,4,5)P3 receptor binding [J].
Chung, SK ;
Shin, BG ;
Chang, YT ;
Suh, BC ;
Kim, KT .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (06) :659-662
[5]   A divergent approach toward synthesis of myo-inositol phosphates: Acyl migrations and regioselectivity [J].
Chung, SK ;
Chang, YT ;
Ryu, YH .
PURE AND APPLIED CHEMISTRY, 1996, 68 (04) :931-935
[6]   REGIOSELECTIVE FUNCTIONALIZATIONS AND CONFORMATIONAL STUDIES OF DI-O-ISOPROPYLIDENE-MYO-INOSITOL DERIVATIVES [J].
CHUNG, SK ;
RYU, YH .
CARBOHYDRATE RESEARCH, 1994, 258 :145-167
[7]  
FERGUSON MAJ, 1988, ANNU REV BIOCHEM, V57, P285
[8]  
GAREGG PJ, 1985, CARBOHYD RES, V139, P209
[9]   THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .18. ALLYL AND BENZYL ETHERS OF MYOINOSITOL - INTERMEDIATES FOR THE SYNTHESIS OF MYOINOSITOL TRISPHOSPHATES [J].
GIGG, J ;
GIGG, R ;
PAYNE, S ;
CONANT, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (02) :423-429
[10]  
GRIGG J, 1997, J CHEM SOC P1, P423