OSMIUM-MEDIATED ASYMMETRIC-SYNTHESIS OF GLYCOSYL-MYO-INOSITOLS FROM OXANORBORNANES

被引：28

作者：

ARJONA, O ^{[1
]}

CANDILEJO, A ^{[1
]}

DEDIOS, A ^{[1
]}

DELAPRADILLA, RF ^{[1
]}

PLUMET, J ^{[1
]}

机构：

[1] CSIC,INST QUIM ORGAN,E-28006 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 23期

关键词：

D O I：

10.1021/jo00049a007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The osmium-catalyzed cis-dihydroxylation of "symmetrical" 4-O-glycosyl-1-O-acetyl-conduritol B derivatives occurs syn to the allyic acetate with high pi-facial selectivity and affords glycosyl-myo-inositols in excellent yield.

引用

页码：6097 / 6099

页数：3

共 41 条

[1] STRAIN-DIRECTED BRIDGE CLEAVAGE OF (PHENYLSULFONYL)-7-OXABICYCLO[2.2.1]HEPTANE DERIVATIVES - APPLICATION TO THE TOTAL SYNTHESIS OF CARBA-ALPHA-DL-GLUCOPYRANOSE [J].

ACENA, JL ;

ARJONA, O ;

DELAPRADILLA, RF ;

PLUMET, J ;

VISO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :1945-1946

[2] THE REGIOSELECTIVE SYNTHESIS OF ENANTIOMERICALLY PURE MYOINOSITOL DERIVATIVES - EFFICIENT SYNTHESIS OF MYOINOSITOL 1,4,5-TRISPHOSPHATE [J].

AGUILO, A ;

MARTINLOMAS, M ;

PENADES, S .

TETRAHEDRON LETTERS, 1992, 33 (03) :401-404

[3] HIGHLY DIASTEREOSELECTIVE BIS-HYDROXYLATION OF A PROTECTED CONDURITOL-B - A SHORT ROUTE TO MYOINOSITOL DERIVATIVES [J].

ARJONA, O ;

DEDIOS, A ;

DELAPRADILLA, RF ;

PLUMET, J .

TETRAHEDRON LETTERS, 1991, 32 (49) :7309-7312

[4] TEMPERATURE-CONTROLLED SYNTHESIS OF 4,7-DIOXATRICYCLO[3.2.1.0(3,6)]OCTANE DERIVATIVES [J].

ARJONA, O ;

DELAPRADILLA, RF ;

PLUMET, J ;

VISO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :772-774

[5] BIOMIMETIC SYNTHESIS OF ENANTIOMERICALLY PURE D-MYO-INOSITOL DERIVATIVES [J].

BENDER, SL ;

BUDHU, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (26) :9883-9885

[6] GLYCOSYL-INOSITOL DERIVATIVES .3. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS [J].

BERLIN, WK ;

ZHANG, WS ;

SHEN, TY .

TETRAHEDRON, 1991, 47 (01) :1-20

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

BILLINGTON, DC .

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

[8] SYNTHESIS OF ALPHA-(1-]2)-, ALPHA-(1-]3)-, ALPHA-(1-]4)-, AND ALPHA-(1-]5)-C-LINKED DISACCHARIDES THROUGH 2,3,4,6-TETRA-O-ACETYLGLUCOPYRANOSYL RADICAL ADDITIONS TO 3-METHYLIDENE-7-OXABICYCLO[2.2.1]HEPTAN-2-ONE DERIVATIVES [J].

BIMWALA, RM ;

VOGEL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2076-2083

[9]

BLOCH R, 1992, J CHEM SOC CHEM COMM, P406

[10] EFFICIENT AND SYSTEMATIC SYNTHESES OF ENANTIOMERICALLY PURE AND REGIOSPECIFICALLY PROTECTED MYOINOSITOLS [J].

BRUZIK, KS ;

TSAI, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6361-6374

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