SYNTHESIS OF (+)-1-DEOXYGALACTONOJIRIMYCIN AND A RELATED INDOLIZIDINE

被引:66
作者
JOHNSON, CR
GOLEBIOWSKI, A
SUNDRAM, H
MILLER, MW
DWAIHY, RL
机构
[1] Department of Chemistry, Wayne State University, Detroit
关键词
D O I
10.1016/0040-4039(94)02343-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amido-alcohol 1 is transformed via aminal 2 into 1-deoxygalactonojirimycin (3) and the structurally related indolizidine 4.
引用
收藏
页码:653 / 654
页数:2
相关论文
共 28 条
[1]   TOTAL SYNTHESES OF GALACTOSIDASE INHIBITORS (+)-GALACTOSTATIN AND (+)-1-DEOXYGALACTOSTATIN [J].
AOYAGI, S ;
FUJIMAKI, S ;
YAMAZAKI, N ;
KIBAYASHI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :815-819
[2]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[3]   SYNTHESIS OF (+)-1,5-DIDEOXY-1,5-IMINO-D-GALACTITOL, A POTENT ALPHA-D-GALACTOSIDASE INHIBITOR [J].
BERNOTAS, RC ;
PEZZONE, MA ;
GANEM, B .
CARBOHYDRATE RESEARCH, 1987, 167 :305-311
[4]  
CHEN YW, 1992, TETRAHEDRON LETT, V33, P4917
[5]   SYNTHESIS OF (+)-GALACTOSTATIN AND (+)-1-DEOXYGALACTOSTATIN UTILIZING L-QUEBRACHITOL AS A CHIRAL BUILDING-BLOCK [J].
CHIDA, N ;
TANIKAWA, T ;
TOBE, T ;
OGAWA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (10) :1247-1248
[6]   STEREOCONTROLLED TOTAL SYNTHESIS OF GALACTOSTATIN FROM SERINE [J].
DONDONI, A ;
MERINO, P ;
PERRONE, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) :1576-1578
[7]  
ELBEIN AD, 1987, ANNU REV BIOCHEM, V56, P497, DOI 10.1146/annurev.biochem.56.1.497
[8]  
ELBEIN AD, 1991, BIOL CARBOHYDRATES, V3, P119
[9]   SYNTHESIS OF A GUANIDINO-SUGAR AS A GLYCOSYL CATION MIMIC [J].
FOTSCH, CH ;
WONG, CH .
TETRAHEDRON LETTERS, 1994, 35 (21) :3481-3484
[10]   SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINO-D-GALACTITOL FROM L-SORBOSE [J].
FURNEAUX, RH ;
TYLER, PC ;
WHITEHOUSE, LA .
TETRAHEDRON LETTERS, 1993, 34 (22) :3609-3612