AN EFFICIENT CONVERSION OF D-MANNITOL INTO D-FRUCTOSE AND 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL (1-DEOXYMANNOJIRIMYCIN)

被引:12
作者
ZOU, W [1 ]
SZAREK, WA [1 ]
机构
[1] QUEENS UNIV,DEPT CHEM,KINGSTON K7L 3N6,ON,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/0008-6215(94)84240-X
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 utility of bis(tributyltin)oxide-bromine for the selective oxidation of secondary hydroxyl groups in the presence of primary hydroxyl groups has been further demonstrated by the efficient conversions of D-mannitol into D-fructose and 1,5-dideoxy-1,5-imino-D-mannitol (1-deoxymannojirimycin).
引用
收藏
页码:25 / 33
页数:9
相关论文
共 31 条
[11]   PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE - SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
WITTY, DR .
TETRAHEDRON, 1989, 45 (01) :319-326
[12]   A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
WITTY, DR .
TETRAHEDRON, 1989, 45 (01) :327-336
[13]   NOVEL MANNOSIDASE INHIBITOR BLOCKING CONVERSION OF HIGH MANNOSE TO COMPLEX OLIGOSACCHARIDES [J].
FUHRMANN, U ;
BAUSE, E ;
LEGLER, G ;
PLOEGH, H .
NATURE, 1984, 307 (5953) :755-758
[14]   PREPARATION AND STORAGE OF (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE (D-GLYCERALDEHYDE ACETONIDE) [J].
HERTEL, LW ;
GROSSMAN, CS ;
KROIN, JS .
SYNTHETIC COMMUNICATIONS, 1991, 21 (02) :151-154
[15]  
HONEYMAN J, 1962, METHODS CARBOHYDR CH, V1, P116
[16]   TAUTOMERIC EQUILIBRIA OF SOME SUGARS BY PARTIALLY RELAXED, C-13 PULSE FOURIER-TRANSFORM, NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
HORTON, D ;
WALASZEK, Z .
CARBOHYDRATE RESEARCH, 1982, 105 (01) :145-153
[17]   A GENERAL-APPROACH TO THE SYNTHESIS OF 2,3-DI-O-PROTECTED DERIVATIVES OF D-GLYCERALDEHYDE [J].
JURCZAK, J ;
BAUER, T ;
CHMIELEWSKI, M .
CARBOHYDRATE RESEARCH, 1987, 164 :493-498
[18]   A 4-STEP SYNTHESIS OF 1-DEOXYNOJIRIMYCIN WITH A BIOTRANSFORMATION AS CARDINAL REACTION STEP [J].
KINAST, G ;
SCHEDEL, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (09) :805-806
[19]   SYNTHESIS OF 5-AMINO-5-DEOXY-D-MANNOPYRANOSE AND 1,5-DI-DEOXY-1,5-IMINO-D-MANNITOL, AND INHIBITION OF ALPHA-D-MANNOSIDASES AND BETA-D-MANNOSIDASES [J].
LEGLER, G ;
JULICH, E .
CARBOHYDRATE RESEARCH, 1984, 128 (01) :61-72
[20]   FORMATION OF 1,5-DIDEOXY-1,5-IMINOHEXITOLS ON BOROHYDRIDE REDUCTION OF 2-AMINO-2-DEOXYHEXOFURANURONO-6,3-LACTONES [J].
LEONTEIN, K ;
LINDBERG, B ;
LONNGREN, J .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (08) :515-518