2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN - AN IMPROVED SYNTHESIS

被引：28

作者：

FURNEAUX, RH

GAINSFORD, GJ

LYNCH, GP

YORKE, SC

机构：

[1] Industrial Research Limited, Lower Hutt

来源：

TETRAHEDRON | 1993年 / 49卷 / 42期

关键词：

D O I：

10.1016/S0040-4020(01)80229-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The potent beta-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.

引用

页码：9605 / 9612

页数：8

共 18 条

[1] CONCISE SYNTHESIS OF 1-DEOXYMANNOJIRIMYCIN
BAXTER, EW
REITZ, AB
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (11) : 1419 - 1422
[2] GLYCOSIDASES IN CANCER AND INVASION
BERNACKI, RJ
NIEDBALA, MJ
KORYTNYK, W
[J]. CANCER AND METASTASIS REVIEWS, 1985, 4 (01) : 81 - 101
[3] THE CHEMISTRY OF THE 1-DEOXYNOJIRIMYCIN SYSTEM - SYNTHESIS OF 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN FROM 1-DEOXYNOJIRIMYCIN
BOSHAGEN, H
HEIKER, FR
SCHULLER, AM
[J]. CARBOHYDRATE RESEARCH, 1987, 164 : 141 - 148
[4] FELLOWS LE, 1989, RECENT ADV PHYTOCHEM, V23, P395
[5] SYNTHESIS OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL AND OF 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL, A POTENT AND SPECIFIC INHIBITOR OF A NUMBER OF BETA-N-ACETYLGLUCOSAMINIDASES
FLEET, GWJ
SMITH, PW
NASH, RJ
FELLOWS, LE
PAREKH, RB
RADEMACHER, TW
[J]. CHEMISTRY LETTERS, 1986, (07) : 1051 - 1054
[6] SYNTHESIS OF DEOXYMANNOJIRIMYCIN FAGOMINE DEOXYNOJIRIMYCIN 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL 2S, 3R, 4R, 5R-TRIHYDROXYPIPECOLIC ACID AND 2S, 3R, 4R, 5S-TRIHYDROXYPIPECOLIC ACID FROM METHYL 3-O-BENZYL-2,6-DIDEOXY-2,6-IMINO-ALPHA-D-MANNOFURANOSIDE
FLEET, GWJ
FELLOWS, LE
SMITH, PW
[J]. TETRAHEDRON, 1987, 43 (05) : 979 - 990
[7] Hahn T., 1983, INT TABLES CRYSTALLO, VA. D
[8] SYNTHESIS OF METHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOFURANOSIDE AND DERIVATIVES
JACQUINE.JC
SINAY, P
[J]. CARBOHYDRATE RESEARCH, 1974, 32 (01) : 101 - 114
[9] ENZYME-CATALYZED ALDOL CONDENSATION FOR ASYMMETRIC-SYNTHESIS OF AZASUGARS - SYNTHESIS, EVALUATION, AND MODELING OF GLYCOSIDASE INHIBITORS
KAJIMOTO, T
LIU, KKC
PEDERSON, RL
ZHONG, ZY
ICHIKAWA, Y
PORCO, JA
WONG, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6187 - 6196
[10] SYNTHESIS AND INHIBITORY PROPERTIES OF 2-ACETAMIDO-2-DEOXYNOJIRIMYCIN (2-ACETAMIDO-5-AMINO-2,5-DIDEOXY-D-GLUCOPYRANOSE, 1) AND 2-ACETAMIDO-1,2-DIDEOXYNOJIRIMYCIN (2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-GLUCITOL,2)
KAPPES, E
LEGLER, G
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (03) : 371 - 388

← 1 2 →