THE REGIOSELECTIVE OPENING OF 5-O-BENZYL-1,2/3,4-O-ISOPROPYLIDENE-D-PSICOFURANOSE WITH ORGANOSTANNANES

被引：0
作者：
DILLON, MP
MAAG, H
MUSZYNSKI, DM
机构：
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 31期
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The trimethylsilyl triflate mediated regioselective opening of 5-O-benzyl-1,2:3,4-O-isopropylidene-D-psicofuranose with organostannanes is presented. Hydrolysis of the initially formed 1-O-trimethylsilyl ether yields the products of S- and C-glycosidation with predominantly beta-stereochemistry in good yields. The unusual addition of acetonitrile to the intermediate oxonium ion when the reaction is performed this medium is also outlined.
引用
收藏
页码：5469 / 5470
页数：2
相关论文
共 11 条
[1]  
DILLON MP, UNPUB
[2]   SYNTHESIS OF 9-(1-DEOXY-1-PHOSPHONO-BETA-D-PSICOFURANOSYL)-1,9-DIHYDRO-6H-PURIN-6-ONE AS A POTENTIAL TRANSITION-STATE ANALOG INHIBITOR OF PURINE NUCLEOSIDE PHOSPHORYLASE [J].
ELLIOTT, RD ;
NIWAS, S ;
RIORDAN, JM ;
MONTGOMERY, JA ;
SECRIST, JA .
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (01) :97-119
[3]   NUCLEIC ACID COMPONENTS AND THEIR ANALOGUES .30. SYNTHESIS OF PSICOFURANINE [J].
FARKAS, J ;
SORM, F .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1963, 28 (04) :882-&
[4]  
Hanessian S, 1976, Adv Carbohydr Chem Biochem, V33, P111
[5]  
HAYASHI M, 1994, HETEROCYCLES, V34, P569
[6]  
HREBABECKY H, 1974, COLLECT CZECH CHEM C, V39, P1098
[7]  
HREBABECKY H, 1974, COLLECT CZECH CHEM C, V39, P2115
[8]   SYNTHETIC STUDIES ON (+)-HYDANTOCIDIN (3) - A NEW SYNTHETIC METHOD FOR CONSTRUCTION OF THE SPIRO-HYDANTOIN RING AT THE ANOMERIC POSITION OF D-RIBOFURANOSE [J].
MIO, S ;
KUMAGAWA, Y ;
SUGAI, S .
TETRAHEDRON, 1991, 47 (12-13) :2133-2144
[9]   HALO SUGAR NUCLEOSIDES .5. SYNTHESIS OF ANGUSTMYCIN A AND SOME BASE ANALOGS [J].
PRISBE, EJ ;
SMEJKAL, J ;
VERHEYDEN, JPH ;
MOFFATT, JG .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1836-1846
[10]   STEREOCONTROLLED SYNTHESIS OF SPIROSUCCINIMIDE DERIVATIVE OF (+)-HYDANTOCIDIN [J].
SANO, H ;
MIO, S ;
TSUKAGUCHI, N ;
SUGAI, S .
TETRAHEDRON, 1995, 51 (05) :1387-1394
12