LEWIS ACID-CATALYZED REARRANGEMENTS OF MYOINOSITOL ORTHOFORMATE DERIVATIVES

被引：38

作者：

GILBERT, IH

HOLMES, AB

PESTCHANKER, MJ

YOUNG, RC

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

[2] SMITHKLINE BEECHAM RES LTD,WELWYN GARDEN CIT AL6 9AR,HERTS,ENGLAND

来源：

CARBOHYDRATE RESEARCH | 1992年 / 234卷

关键词：

D O I：

10.1016/0008-6215(92)85043-Y

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) With di isobytylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-inositol (6). 2,4,5,6-Tetra-O-benzyl-1,3-O-methylene-DL-myo-inositol (16) reacted with allyltrimethylsilane in the presence of Lewis acids to give 2,4,5,6-tetra-0-benzyl-1-O-(3-butenyl)-DL-myo-inositol [(+/-)-17] or rearranged to give 4,5,6-tri-O-benzyl-1,2-0-methylene-DL-myo-inositol [+/-)-18].

引用

收藏

页码：117 / 130

页数：14

相关论文

共 35 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2] PDGF-DEPENDENT TYROSINE PHOSPHORYLATION STIMULATES PRODUCTION OF NOVEL POLYPHOSPHOINOSITIDES IN INTACT-CELLS [J].

AUGER, KR ;

SERUNIAN, LA ;

SOLTOFF, SP ;

LIBBY, P ;

CANTLEY, LC .

CELL, 1989, 57 (01) :167-175

[3] ACETOLYSIS OF CYCLIC ACETALS - REGIOSELECTIVE ACYLATIVE CLEAVAGE OF CYCLIC FORMALS [J].

BAILEY, WF ;

RIVERA, AD .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (25) :4958-4964

[4] REACTION OF 2-METHOXY-1,3-DIOXANE WITH GRIGNARD-REAGENTS - REAGENT-SUBSTRATE COMPLEXATION AND STEREOELECTRONIC CONTROL [J].

BAILEY, WF ;

CROTEAU, AA .

TETRAHEDRON LETTERS, 1981, 22 (06) :545-548

[5] CONFORMATIONAL CHANGE OCCASIONED BY COMPLEXATION - CONTRA-ANOMERIC-EFFECT EPIMERIZATION OF 2-METHOXY-1,3-DIOXANES IN THE PRESENCE OF MAGNESIUM BROMIDE [J].

BAILEY, WF ;

RIVERA, AD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1559-1562

[6] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .3. ON THE STEREOCHEMISTRY OBSERVED IN THE CYCLIZATION OF CHIRAL ACETALS OF POLYOLEFINIC ALDEHYDES - FORMATION OF OPTICALLY-ACTIVE HOMOALLYLIC ALCOHOLS [J].

BARTLETT, PA ;

JOHNSON, WS ;

ELLIOTT, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2088-2089

[7] INOSITOL PHOSPHATES AND CELL SIGNALING [J].

BERRIDGE, MJ ;

IRVINE, RF .

NATURE, 1989, 341 (6239) :197-205

[8] SYNTHESIS OF MYOINOSITOL 1,3,4,5-TETRAPHOSPHATE AND MYOINOSITOL 1,3-BISPHOSPHATE [J].

BILLINGTON, DC ;

BAKER, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :1011-1013

[9] THE TOTAL SYNTHESIS OF MYOINOSITOL PHOSPHATES VIA MYOINOSITOL ORTHOFORMATE [J].

BILLINGTON, DC ;

BAKER, R ;

KULAGOWSKI, JJ ;

MAWER, IM ;

VACCA, JP ;

DESOLMS, SJ ;

HUFF, JR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1423-1429

[10] RECENT DEVELOPMENTS IN THE SYNTHESIS OF MYOINOSITOL PHOSPHATES [J].

BILLINGTON, DC .

CHEMICAL SOCIETY REVIEWS, 1989, 18 (01) :83-122

← 1 2 3 4 →