Stereoselective synthesis of arabinose-derived phosphonates

被引：39

作者：

Bouix, C ^{[1
]}

Bisseret, P ^{[1
]}

Eustache, J ^{[1
]}

机构：

[1] Univ Haute Alsace, Ecole Natl Super Chim Mulhouse, CNRS, Lab Synth Organ & Chim Microbienne, F-68093 Mulhouse, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 08期

关键词：

D O I：

10.1016/S0040-4039(97)10723-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, stereoselective synthesis of three new azasugar-derived phosphonates is described. The new compounds are versatile intermediates for the synthesis of glycosyltransferase inhibitors. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：825 / 828

页数：4

共 13 条

[1] Synthesis of (difluoromethyl)phosphonate azasugars designed as inhibitors for glycosyl transferases [J].

Behr, JB ;

Evina, CM ;

Phung, N ;

Guillerm, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1597-1599

[2] The embAB genes of Mycobacterium avium encode an arabinosyl transferase involved in cell wall arabinan biosynthesis that is the target for the antimycobacterial drug ethambutol [J].

Belanger, AE ;

Besra, GS ;

Ford, ME ;

Mikusova, K ;

Belisle, JT ;

Brennan, PJ ;

Inamine, JM .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (21) :11919-11924

[3] Stereoselective synthesis of the isosteric phosphono analogues of N-acetyl-alpha-D-glucosamine 1-phosphate and N-acetyl-alpha-D-mannosamine 1-phosphate [J].

Casero, F ;

Cipolla, L ;

Lay, L ;

Nicotra, F ;

Panza, L ;

Russo, G .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3428-3432

[4]

CHORGADE MS, 1994, TETRAHEDRON ASYMETRY, V11, P2251

[5] Easy and stereoselective synthesis of the phosphono analogue of alpha-L-rhamnose 1-phosphate [J].

Cipolla, L ;

LaFerla, B ;

Nicotra, F ;

Panza, L .

TETRAHEDRON LETTERS, 1997, 38 (31) :5567-5568

[6] EPIMERIZATION AT C-2 DURING THE WITTIG REACTION OF 2,3,5-TRI-O-BENZYL-D-RIBOSE AND METHYLIDENETRIPHENYLPHOSPHORANE [J].

FREEMAN, F ;

ROBARGE, KD .

CARBOHYDRATE RESEARCH, 1986, 154 :270-274

[7] THE TAUTOMERISM OF A PHOSPHONO ENAMINE [J].

HIGHET, RJ ;

JONES, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :4038-4040

[8] Cyclic guanidino-sugars with low pK(a) as transition-state analog inhibitors of glycosidases: Neutral instead of charged species are the active forms [J].

Jeong, JH ;

Murray, BW ;

Takayama, S ;

Wong, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (18) :4227-4234

[9] Synthesis of 9-[2',3'-dideoxy-2',3'-bis-C-hydroxymethyl-alpha-L-threofuranosyl] adenine and its 4'-thio analog as potential antiviral agents [J].

Kikuchi, Y ;

Kurata, H ;

Nishiyama, S ;

Yamamura, S ;

Kato, K .

TETRAHEDRON LETTERS, 1997, 38 (27) :4795-4798

[10] SYNTHESIS OF THE MYCOBACTERIAL ARABINOSE DONOR BETA-D-ARABINOFURANOSYL-1-MONOPHOSPHORYLDECAPRENOL, DEVELOPMENT OF A BASIC ARABINOSYL-TRANSFERASE ASSAY, AND IDENTIFICATION OF ETHAMBUTOL AS AN ARABINOSYL TRANSFERASE INHIBITOR [J].

LEE, RE ;

MIKUSOVA, K ;

BRENNAN, PJ ;

BESRA, GS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) :11829-11832

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