PREPARATION OF 2-AZIDO-4-O-BENZOYL-2,6-DIDEOXY-3-O-METHYL-BETA-D-ALLOPYRANOSE AND ITS DISACCHARIDE DERIVATIVE

被引:1
作者
WANG, F [1 ]
SAKAIRI, N [1 ]
KUZUHARA, H [1 ]
机构
[1] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN
关键词
D O I
10.1080/07328309308020097
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
2-Azido-4-O-benzoyl-2,6-dideoxy-3-O-methyl-D-allopyranose, needed as one of the building blocks for construction of a novel cyclodextrin-like compound, was prepared in the form of crystalline beta-anomer 6 from methyl 2-azido-4,6-O-benzylidene-2-deoxy-alpha-D-allopyranoside 1. As a model of alpha-glycosidation necessary for formation of a cyclic structure, 6 was converted into the corresponding beta-glycosyl trichloroacetimidate and coupled with methyl 6-O-benzyl-2,3-di-O-methyl-alpha-D-glucopyranoside 8, giving alpha(1-->4)-linked disaccharide derivative 9.
引用
收藏
页码:823 / 831
页数:9
相关论文
共 50 条
[41]   PREPARATION AND STRUCTURAL DETERMINATION OF METHYL 4,6-O-BENZYLIDENE-2,3-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOSID[2,3-D]TRIAZOLE AND OF ITS ADDUCTS WITH 3-NITROHEX-2-ENOPYRANOSIDES [J].
SAKAKIBARA, T ;
NAKAGAWA, T ;
FUNABASHI, M .
CARBOHYDRATE RESEARCH, 1987, 168 (01) :47-53
[42]   SYNTHESIS OF BENZYL 2-AZIDO-2-DEOXY-4-O-BETA-D-GLUCOPYRANOSYL-ALPHA-D-GLUCOPYRANOSIDE AND 1,6-ANHYDRO-2-AZIDO-2-DEOXY-4-O-BETA-D-GLUCOPYRANOSYL-BETA-D-GLUCOPYRANOSE [J].
SHING, TKM ;
PERLIN, AS .
CARBOHYDRATE RESEARCH, 1984, 130 (JUL) :65-72
[43]   SYNTHESIS OF METHYL BETA-D-LYXOFURANOSIDE DERIVATIVES FROM METHYL 2,3-DI-O-SULFONYLOXY-5-O-BENZOYL-BETA-D-RIBOFURANOSIDE [J].
HILDESHE.J ;
CLEOPHAX, J ;
GERO, SD .
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1968, 267 (17) :1070-&
[44]   SYNTHESIS OF 1,6-ANHYDRO-2-O-BENZOYL-3,4-DIDEOXY-BETA-D-ERYTHRO-HEX-3-ENOPYRANOSE [J].
CHEETHAM, NWH .
CARBOHYDRATE RESEARCH, 1978, 63 (JUN) :293-296
[45]   PREPARATION OF METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-3-DEOXY-3-NITRO-BETA-D-ALLOPYRANOSIDE AND SOME C2-BRANCHED-CHAIN DERIVATIVES OF METHYL 4,6-O-BENZYLIDENE-2,3-DIDEOXY-3-NITRO-BETA-D-GLUCOPYRANOSIDE [J].
SAKAKIBARA, T ;
KUMAZAWA, S ;
NAKAGAWA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (08) :2655-+
[46]   STUDIES IN OLIGOSACCHARIDE CHEMISTRY .6. SYNTHESIS OF A DISACCHARIDE OXAZOLINE - 2-METHYL-[4,6-DI-O-ACETYL-1,2-DIDEOXY-3-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GLUCOPYRANO] [2',1'-4,5]-2-OXAZOLINE [J].
AUGE, C ;
VEYRIERES, A .
CARBOHYDRATE RESEARCH, 1976, 46 (02) :293-298
[47]   SYNTHESIS OF THE CAPSULAR POLYSACCHARIDE OF STREPTOCOCCUS-PNEUMONIAE TYPE-14 .2. SYNTHESIS OF METHYL 6-O-ACETYL-3-O-BENZOYL-4-O-(2,3,4,6-TETRA-O-BENZOYL-BETA-D-GALACTOPYRANOSYL)-2-DEOXY-2-PHTHALIMIDO-BETA-D-GLYCOPYRANOSIDE, A LACTOSAMINE PRECURSOR OF A MONOMER FOR POLYCONDENSATION [J].
NIFANTEV, NE ;
BACKINOWSKY, LV ;
KOCHETKOV, NK .
BIOORGANICHESKAYA KHIMIYA, 1987, 13 (07) :977-991
[48]   Methyl 3-O-benzoyl-4,6-O-benzylidene-2-O-trifluoromethylsulfonyl-alpha-D-mannopyranoside [J].
Barnes, JC ;
Brimacombe, JS ;
Kabir, AKMS .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :416-418
[49]   CHEMISTRY OF CELLOBIOSE AND LACTOSE .5. TRANSFORMATION OF LACTOSE INTO ITS 3-EPIMER 4-O-BETA-D-GALACTOPYRANOSYL-D-ALLOPYRANOSE [J].
BHATT, RS ;
HOUGH, L ;
RICHARDSON, AC .
CARBOHYDRATE RESEARCH, 1976, 51 (02) :272-275
[50]   A SIMPLE PREPARATION OF METHYL 2,6-DIDEOXY-ALPHA-D-ARABINO-HEXOPYRANOSIDE AND METHYL 3,6-DIDEOXY-ALPHA-D-ARABINO-HEXOPYRANOSIDE BY PHOTOCHEMICAL DEOXYGENATION [J].
KLAUSENER, A ;
MULLER, E ;
RUNSINK, J ;
SCHARF, HD .
CARBOHYDRATE RESEARCH, 1983, 116 (02) :295-302