Stereospecific synthesis of β-D-allopyrano sides by dihydroxylation of β-D-erythro-2,3-dideoxyhex-2-enopyranosides

被引:19
作者
Murphy, PV [1 ]
O'Brien, JL
Smith, AB
机构
[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Conway Inst Biomol & Biomed Res, Dublin 4, Ireland
[2] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
stereospecific synthesis; beta-D-allopyranoside; dihydroxylation; beta-D-erythro-2,3-Dideoxyhex-2-enopyrano sides; inversion of configuration;
D O I
10.1016/S0008-6215(01)00181-1
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
The synthesis of 4,6-O-benzylidene-beta -D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give beta -D-allopyranosides in moderate to excellent yield. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:327 / 335
页数:9
相关论文
共 26 条
[11]   DE-NOVO DESIGN AND SYNTHESIS OF SOMATOSTATIN NONPEPTIDE PEPTIDOMIMETICS UTILIZING BETA-D-GLUCOSE AS A NOVEL SCAFFOLDING [J].
HIRSCHMANN, R ;
NICOLAOU, KC ;
PIETRANICO, S ;
LEAHY, EM ;
SALVINO, J ;
ARISON, B ;
CICHY, MA ;
SPOORS, PG ;
SHAKESPEARE, WC ;
SPRENGELER, PA ;
HAMLEY, P ;
SMITH, AB ;
REISINE, T ;
RAYNOR, K ;
MAECHLER, L ;
DONALDSON, C ;
VALE, W ;
FREIDINGER, RM ;
CASCIERI, MR ;
STRADER, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12550-12568
[12]   PERIODATE OXIDATION .4. THE EFFECT OF CONFORMATION OF CYCLIC GLYCOLS ON THE RATE OF PERIODATE OXIDATION [J].
HONEYMAN, J ;
SHAW, CJG .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (JUL-A) :2454-2465
[14]   A NEW SYNTHESIS OF METHYL-2,3-DIDESOXY ALPHA D-ERYTHRO-HEX-2-ENOPYRANOSIDE [J].
KLEMER, A ;
MERSMANN, G .
CARBOHYDRATE RESEARCH, 1970, 12 (02) :219-&
[15]   REACTIONS OF SOME PYRANOSIDE DIOL MONOTRIFLATES WITH NUCLEOPHILES AND BASES [J].
KNAPP, S ;
NAUGHTON, ABJ ;
JARAMILLO, C ;
PIPIK, B .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7328-7334
[16]   A NOVEL ROUTE TO OLEFINS FROM VICINAL DIOLS [J].
LIU, ZC ;
CLASSON, B ;
SAMUELSSON, B .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4273-4275
[17]   Syntheses of 5′-O-glycosylnucleosides [J].
Liu, ZJ ;
Zhou, M ;
Min, JM ;
Zhang, LH .
TETRAHEDRON-ASYMMETRY, 1999, 10 (11) :2119-2127
[18]   GLYCOSYLIDENE CARBENES .15. SYNTHESIS OF DISACCHARIDES FROM ALLOPYRANOSE-DERIVED VICINAL 1,2-DIOLS - EVIDENCE FOR THE PROTONATION BY A H-BONDED HYDROXY GROUP IN THE DELTA-PLANE OF THE INTERMEDIATE CARBENE, FOLLOWED BY ATTACK ON THE OXYCARBENIUM ION IN THE PI-PLANE [J].
MUDDASANI, PR ;
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1994, 77 (01) :334-350
[19]   FORMATION OF GLYCOSIDES BY EPOXIDATION-RING CLOSURE OF OPEN-CHAIN HYDROXYENOL ETHERS OBTAINED FROM SUGARS [J].
NICOTRA, F ;
PANZA, L ;
RONCHETTI, F ;
RUSSO, G ;
TOMA, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (06) :1319-1324
[20]   Ruthenium-catalyzed cis-dihydroxylation of alkenes: Scope and limitations [J].
Shing, TKM ;
Tam, EKW ;
Tai, VWF ;
Chung, IHF ;
Jiang, Q .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (01) :50-57