A SHORT SYNTHESIS OF SUBSTITUTED BETA-HYDROXY GAMMA-BUTYROLACTONES AND 2-DEOXYHEXOFURANOSIDES

被引：19

作者：

ESCUDIER, JM ^{[1
]}

BALTAS, M ^{[1
]}

GORRICHON, L ^{[1
]}

机构：

[1] UNIV TOULOUSE 3,SYNTHESE & PHYSICOCHIM ORGAN LAB,CNRS,118 ROUTE NARBONNE,F-31062 TOULOUSE,FRANCE

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 11期

关键词：

GAMMA-DELTA-EPOXY BETA-HYDROXYESTERS; LACTONIZATION; 2-DEOXYHEXOSES;

D O I：

10.1016/S0040-4039(00)91641-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The gamma,delta-epoxy beta-hydroxyestes obtained by diastereoselective aldolisation beetwen ester enolates and optically active alpha,beta-epoxyaldehydes, undergo quantitative stereocontrolled lactonisation which can be followed by reduction to provide 2-deoxy hexofuranosides.

引用

页码：1439 / 1442

页数：4

共 14 条

[1]

Bollit V., 1990, J ORG CHEM, V55, P5812

[2] ON THE STRAIN-ENERGY OF 5-RING AND 6-RING LACTONES [J].

BROWN, JM ;

CONN, AD ;

PILCHER, G ;

LEITAO, MLP ;

YANG, MY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1817-1819

[3] GENERAL SYNTHETIC ROUTES TO BETA-HYDROXY-ACIDS FROM TERTIARY-BUTYL ESTERS AND REFORMATSKII REACTION [J].

CORNFORTH, DA ;

OPARA, AE ;

READ, G .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19) :2799-+

[4] DIASTEREOSELECTION IN THE ADDITION OF ENOLATES TO CHIRAL ALPHA,BETA-EPOXYALDEHYDES [J].

ESCUDIER, JM ;

BALTAS, M ;

GORRICHON, L .

TETRAHEDRON LETTERS, 1991, 32 (39) :5345-5348

[5] SYNTHESIS OF 3'-AZIDO-5'-HOMOTHYMIDINE ANALOGS [J].

GAUTIER, C ;

LEROY, R ;

MONNERET, C ;

ROGER, P .

TETRAHEDRON LETTERS, 1991, 32 (28) :3361-3364

[6] FORMATION OF CONVENIENT CHIRAL INTERMEDIATES FROM CARBOHYDRATES AND THEIR USE IN SYNTHESIS [J].

INCH, TD .

TETRAHEDRON, 1984, 40 (17) :3161-3213

[7] 5-MEMBERED, 4-MEMBERED, AND 3-MEMBERED CARBOCYCLIC RINGS FROM 2-DEOXYRIBOSE BY INTRAMOLECULAR NUCLEOPHILIC DISPLACEMENT REACTION [J].

KROHN, K ;

BORNER, G .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6038-6043

[8] SYNTHESIS OF 1-(2,3-DIDEOXY-2-FLUORO-BETA-D-THREO-PENTOFURANOSYL)CYTOSINE (F-DDC) - A PROMISING AGENT FOR THE TREATMENT OF ACQUIRED-IMMUNE-DEFICIENCY-SYNDROME [J].

OKABE, M ;

SUN, RC ;

ZENCHOFF, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14) :4392-4397

[9]

POLL R, 1991, TETRAHEDRON LETT, V32, P4831

[10] STEREOSELECTIVE SYNTHESIS OF 3-(ETHOXYCARBONYL)-4-HYDROXY-5-(1-HYDROXYALKYL)-2-ISOXAZOLINE 2-OXIDES BY REACTION OF 2,3-EPOXY ALDEHYDES AND ETHYL NITROACETATE ON ALUMINA SURFACE [J].

ROSINI, G ;

GALARINI, R ;

MAROTTA, E ;

RIGHI, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :781-783

← 1 2 →