SYNTHESIS OF ALPHA-HOMOGALACTOSTATIN AND OF ITS 1,N-ANHYDRO DERIVATIVE

被引：26

作者：

MARTIN, OR

XIE, F

LIU, L

机构：

[1] Department of Chemistry, State University of New York, Binghamton

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 23期

关键词：

D O I：

10.1016/0040-4039(95)00708-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Homogalactostatin 2 was prepared in 10 steps from 2,3,4,6-tetra-O-benzyl-D-galactose by way of a Wittig chain extension and a mercuricyclization. The synthesis of 2 was assisted by the unexpected participation of the nitrogen protecting group (benzyl carbamate) during iododemercuration. Intermediate 10 was converted in 2 steps into the 1,N-anhydro derivative of 2, compound 3, a potential inactivator of galactosidases.

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页码：4027 / 4030

页数：4

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共 31 条

[1] SYNTHESIS OF AND GLYCOSIDASE INHIBITION BY ALPHA-L-HOMOFUCONOJIRIMYCIN [J].

ANDREWS, DM ;

BIRD, MI ;

CUNNINGHAM, MM ;

WARD, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (12) :2533-2536

[2] 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

[3] ANALOGS OF SIALIC ACIDS AS POTENTIAL SIALIDASE INHIBITORS - SYNTHESIS OF 2-C-HYDROXYMETHYL DERIVATIVES OF N-ACETYL-6-AMINO-2,6-DIDEOXY-NEURAMINIC ACID [J].

BERNET, B ;

MURTY, ARCB ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1990, 73 (04) :940-958

[4] 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

[5] EFFICIENT PREPARATION OF ENANTIOMERICALLY PURE CYCLIC AMINOALDITOLS, TOTAL SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN [J].

BERNOTAS, RC ;

GANEM, B .

TETRAHEDRON LETTERS, 1985, 26 (09) :1123-1126

[6] VINYLATION ELECTROPHILIC CYCLIZATION OF ALDOPENTOSES - EASY AND STEREOSELECTIVE ACCESS TO C-GLYCOPYRANOSIDES OF RARE SUGARS [J].

BOSCHETTI, A ;

NICOTRA, F ;

PANZA, L ;

RUSSO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (18) :4181-4185

[7] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF ALPHA-HOMOMANNOJIRIMYCIN, 6-EPI-ALPHA-HOMOMANNOJIRIMYCIN AND OF A HIGHLY SUBSTITUTED PIPECOLIC ACID [J].

BRUCE, I ;

FLEET, GWJ ;

DIBELLO, IC ;

WINCHESTER, B .

TETRAHEDRON, 1992, 48 (46) :10191-10200

[8] THE UTILITY OF 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL AS A PFP ENZYME-INHIBITOR [J].

CHORGHADE, MS ;

CSEKE, CT ;

LIU, PS .

TETRAHEDRON-ASYMMETRY, 1994, 5 (11) :2251-2254

[9] EFFECT OF THE ACIDIC COMPONENT ON THE MITSUNOBU INVERSION OF A STERICALLY HINDERED ALCOHOL [J].

DODGE, JA ;

TRUJILLO, JI ;

PRESNELL, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :234-236

[10] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF AND SPECIFIC ALPHA-L-FUCOSIDASE INHIBITION BY BETA-L-HOMOFUCONOJIRIMYCIN AND 1-BETA-C-SUBSTITUTED DEOXYMANNOJIRIMYCINS [J].

FLEET, GWJ ;

NAMGOONG, SK ;

BARKER, C ;

BAINES, S ;

JACOB, GS ;

WINCHESTER, B .

TETRAHEDRON LETTERS, 1989, 30 (33) :4439-4442

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