Total synthesis of 1,3-dideoxynojirimycin

被引:13
作者
Gryko, D
Jurczak, J
机构
[1] POLISH ACAD SCI,INST ORGAN CHEM,PL-01224 WARSAW,POLAND
[2] WARSAW UNIV,DEPT CHEM,PL-02093 WARSAW,POLAND
关键词
D O I
10.1016/S0040-4039(97)10166-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of allyl bromide (5) to N-benzyl-N-carbobenzoxy-O-tert-butyldimethyl-D-serinal (4) afforded with high diastereoselectivity anti-adduct 6 which subsequently transformed into(2R,4S,5R)-1,3-dideoxynojirimycin (1). (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8275 / 8278
页数:4
相关论文
共 22 条
[11]   RATIONAL DESIGN OF AZA SUGARS VIA BIOCATALYSIS - MANNOJIRIMYCIN AND OTHER GLYCOSIDASE INHIBITORS [J].
HUDLICKY, T ;
ROUDEN, J ;
LUNA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :985-987
[12]  
IMAI T, 1993, SYNTHESIS-STUTTGART, P395
[13]  
Jarosz S., 1992, POLISH J CHEM, V66, P1853
[14]   CHEMOENZYMATIC SYNTHESIS OF 1,3-DIDEOXYNOJIRIMYCIN [J].
JOHNSON, CR ;
GOLEBIOWSKI, A ;
BRAUN, MP ;
SUNDRAM, H .
TETRAHEDRON LETTERS, 1994, 35 (12) :1833-1834
[15]   HIGHLY STEREOSELECTIVE SYNTHESIS OF CIS-(2R,3S)-3-HYDROXYPROLINE [J].
JURCZAK, J ;
PROKOPOWICZ, P ;
GOLEBIOWSKI, A .
TETRAHEDRON LETTERS, 1993, 34 (44) :7107-7110
[16]   OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS [J].
JURCZAK, J ;
GOLEBIOWSKI, A .
CHEMICAL REVIEWS, 1989, 89 (01) :149-164
[17]  
JURCZAK J, UNPUB TETRAHEDRON LE
[18]  
KICIAK K, 1994, POLISH J CHEM, V68, P19
[19]  
LEANNA MR, 1992, TETRAHEDRON LETT, V33, P5029
[20]   SYNTHESIS OF 5-FLUORO-PROSTAGLANDINS [J].
NAKAI, H ;
HAMANAKA, N ;
MIYAKE, H ;
HAYASHI, M .
CHEMISTRY LETTERS, 1979, (12) :1499-1502