A SIMPLE SYNTHESIS OF ALL 4 STEREOISOMERS OF 2,2,5-TRIMETHYL-1,3-DIOXOLANE-4-CARBALDEHYDE

被引：4

作者：

BINDER, WH

PRENNER, RH

SCHMID, W

机构：

来源：

MONATSHEFTE FUR CHEMIE | 1994年 / 125卷 / 6-7期

关键词：

2,2,5-TRIMETHYL-1,3-DIOXOLANE-4-CARBALDEHYDES; ALDOPENTOSE DIETHYL DITHIOACETALS; LEAD TETRAACETATE CLEAVAGE;

D O I：

10.1007/BF01277638

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient procedure for the syntheses of all four stereoisomers of the 2,2,5-trimethyl-1,3-dioxolane-4-carbaldehydes 1a-1d has been developed. Starting with readily available aldopentose diethyl dithioacetals 2, 6, 10 and 14, the title compounds were obtained by a selective protecting group strategy and subsequent Raney-nickel reduction, followed by lead tetraacetate cleavage. This procedure allows an application on a multigram scale.

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页码：763 / 771

页数：9

相关论文

共 22 条

[1]

BERNARDI R, 1980, SYNTHESIS, V50

[2] INDIUM-MEDIATED ALLYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO 2-DEOXY AND 2,6-DIDEOXY CARBOHYDRATES [J].

BINDER, WH ;

PRENNER, RH ;

SCHMID, W .

TETRAHEDRON, 1994, 50 (03) :749-758

[3] TOTAL SYNTHESIS OF (+/-)-CITREOVIRAL, BASED ON A BIOGENETIC MODEL, AND FORMAL SYNTHESIS OF (+/-)-CITREOVIRIDIN [J].

BOWDEN, MC ;

PATEL, P ;

PATTENDEN, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08) :1947-1950

[4] ITERATIVE, STEREOSELECTIVE HOMOLOGATION OF CHIRAL POLYALKOXY ALDEHYDES EMPLOYING 2-(TRIMETHYLSILYL)THIAZOLE AS A FORMYL ANION EQUIVALENT - THE THIAZOLE ROUTE TO HIGHER CARBOHYDRATES [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

MEDICI, A ;

PEDRINI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :693-702

[5] REGIOSELECTIVE AND STEREOSELECTIVE CONJUGATE ADDITION OF NITROGEN NUCLEOPHILES TO 2-ALKENYL N-METHYLTHIAZOLIUM IODIDES - SYNTHESIS OF D-3-EPI-DAUNOSAMINE AND SOME LINCOSAMINE ANALOGS [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

MERINO, P .

TETRAHEDRON, 1990, 46 (17) :6167-6184

[6] STEREOCHEMISTRY AND SYNTHETIC APPLICATIONS OF THE PRODUCTS OF YEAST REDUCTION OF 3-HYDROXY-3-METHYL-5-PHENYLPENT-4-EN-2-ONE [J].

FRONZA, G ;

FUGANTI, C ;

PEDROCCHIFANTONI, G ;

SERVI, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1141-1144

[7] ON THE STERIC COURSE OF THE ADDITION OF DIALLYLZINC ONTO ALPHA,BETA-DIALKOXY CHIRAL CARBONYL-COMPOUNDS - STEREOSPECIFIC SYNTHESIS OF 2,6-DIDEOXYSUGARS OF THE L-SERIES [J].

FRONZA, G ;

FUGANTI, C ;

GRASSELLI, P ;

PEDROCCHIFANTONI, G ;

ZIROTTI, C .

TETRAHEDRON LETTERS, 1982, 23 (40) :4143-4146

[8] SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL [J].

FUGANTI, C ;

GRASSELLI, P ;

SERVI, S ;

ZIROTTI, C .

TETRAHEDRON LETTERS, 1982, 23 (41) :4269-4272

[9] SYNTHESIS OF N-BENZOYL-L-DAUNOSAMINE FROM D-THREONINE [J].

FUGANTI, C ;

GRASSELLI, P ;

PEDROCCHIFANTONI, G .

TETRAHEDRON LETTERS, 1981, 22 (40) :4017-4020

[10]

GRINDLEY TB, 1987, CARBOHYD RES, V167, P105