Syntheses of deoxyhexoses from diastereoisomerically pure hetero-Diels-Alder adduct

被引:21
作者
Bauer, T
机构
[1] University of Warsaw, Department of Chemistry, Pasteura 1
关键词
D O I
10.1016/S0040-4020(97)00159-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses of deoxyhexoses are presented. The concept is based on the functionalization of enantiomerically pure 6-hydroxymethyl-2-methoxy-5,6-dihydro-2H-pyran, which is easily synthesized by asymmetric hetero-Diels-Alder reaction. Methyl 4,6-dideoxy-alpha-D-arabino-hexopyranoside, methyl alpha-D-chalcoside and methyl alpha-D-desosanimide are synthesized. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4763 / 4768
页数:6
相关论文
共 17 条
[11]  
OPPOLZER W, 1990, PURE APP CHEM, V62, P1
[12]   SYNTHESIS OF DESOSAMINE HYDROCHLORIDE [J].
RICHARDSON, AC .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (DEC) :5364-&
[13]  
STILL WC, 1978, J ORG CHEM, V43, P2939
[14]   STEREOSPECIFIC SYNTHESIS OF C-9-C-16 SEGMENT OF CARBONOLIDE-B, A GLYCON OF CARBOMYCIN-B [J].
TATSUTA, K ;
YAMAUCHI, T ;
KINOSHITA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (10) :3035-3038
[15]  
WOO WKP, 1962, J AM CHEM SOC, V84, P1066
[16]   THE SYNTHESIS OF SUGARS FROM NON-CARBOHYDRATE SUBSTRATES [J].
ZAMOJSKI, A ;
BANASZEK, A ;
GRYNKIEWICZ, G .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1982, 40 :1-129
[17]  
Zamojski A, 1984, TOTAL SYNTHESIS NATU, V6, P141