A general strategy towards the synthesis of 1-N-iminosugar type glycosidase inhibitors:: demonstration by the synthesis of D- as well as L-glucose type iminosugars (isofagomines)

被引：45

作者：

Pandey, G ^{[1
]}

Kapur, M ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Synth, Poona 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)01553-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of isofagomine, the potent glycosidase inhibitor of a type 1-N-iminosugar have been synthesized by the intramolecular cyclization of the PET generated alpha -trimethylsilylmethylamine radical cation with the appropriate tethered acetylene moiety. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：8821 / 8824

页数：4

共 15 条

[1] A FACILE, PRACTICAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL (MDL 25,637) [J].

ANZEVENO, PB ;

CREEMER, LJ ;

DANIEL, JK ;

KING, CHR ;

LIU, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2539-2542

[2] ACARBOSE - AN UPDATE OF ITS PHARMACOLOGY AND THERAPEUTIC USE IN DIABETES-MELLITUS [J].

BALFOUR, JA ;

MCTAVISH, D .

DRUGS, 1993, 46 (06) :1025-1054

[3]

COREY EJ, 1972, TETRAHEDRON LETT, P3769

[4] Glycobiology: Toward understanding the function of sugars [J].

Dwek, RA .

CHEMICAL REVIEWS, 1996, 96 (02) :683-720

[5]

GROSS PE, 1995, CLIN CANCER RES, V1, P935

[6]

HUGHS AB, 1994, J NAT PROD REP, P35

[7] 1-N-iminosugars:: Potent and selective inhibitors of β-glycosidases [J].

Ichikawa, Y ;

Igarashi, Y ;

Ichikawa, M ;

Suhara, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (13) :3007-3018

[8] TOTAL SYNTHESIS OF (+)-NOJIRIMYCIN AND (+)-1-DEOXYNOJIRIMYCIN [J].

IIDA, H ;

YAMAZAKI, N ;

KIBAYASHI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3337-3342

[9] ISOFAGOMINE, A POTENT, NEW GLYCOSIDASE INHIBITOR [J].

JESPERSEN, TM ;

DONG, WL ;

SIERKS, MR ;

SKRYDSTRUP, T ;

LUNDT, I ;

BOLS, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (17) :1778-1779

[10] Highly selective synthesis of 1-N-iminosugars of the D-glucose and -glucuronic acid types [J].

Kim, YJ ;

Ichikawa, M ;

Ichikawa, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2599-2602

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