A short route to α-chloro- and α-azido-ulosonic esters

被引：19

作者：

Lakhrissi, M ^{[1
]}

Chapleur, Y ^{[1
]}

机构：

[1] Univ Nancy 1, CNRS, UMR 7565, Grp SUCRES, F-54506 Vandoeuvre Les Nancy, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(98)00872-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two step route to alpha-chloro-ulosonic esters from lactones involving the reaction of dichloroolefins with m-chloroperbenzoic acid in dichloromethane is described. Subsequent substitution of chlorine by the azide ion yields the corresponding anomeric azido-esters, which may be useful intermediates for the preparation of "anomeric amino-acids" and related compounds. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4659 / 4662

页数：4

共 24 条

[1] DICHLOROMETHYLENATION OF 1,4-LACTONES - A NEW ACCESS TO 1-DEOXY-1-C-METHYL-C-GLYCOSYL COMPOUNDS [J].

BANDZOUZI, A ;

CHAPLEUR, Y .

CARBOHYDRATE RESEARCH, 1987, 171 :13-24

[2] POTENT INHIBITION OF GLYCOGEN-PHOSPHORYLASE BY A SPIROHYDANTOIN OF GLUCOPYRANOSE - FIRST PYRANOSE ANALOGS OF HYDANTOCIDIN [J].

BICHARD, CJF ;

MITCHELL, EP ;

WORMALD, MR ;

WATSON, KA ;

JOHNSON, LN ;

ZOGRAPHOS, SE ;

KOUTRA, DD ;

OIKONOMAKOS, NG ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1995, 36 (12) :2145-2148

[3] Glucofuranose analogues of hydantocidin [J].

Brandstetter, TW ;

delaFuente, C ;

Kim, YH ;

Johnson, LN ;

Crook, S ;

Lilley, PMDQ ;

Watkin, DJ ;

Tsitsanou, KE ;

Zographos, SE ;

Chrysina, ED ;

Oikonomakos, NG ;

Fleet, GWJ .

TETRAHEDRON, 1996, 52 (32) :10721-10736

[4] A CONVENIENT SYNTHESIS OF SUBSTITUTED CHIRAL TETRAHYDROFURANS FROM SUGAR GAMMA-LACTONES [J].

CHAPLEUR, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (07) :449-450

[5]

CHAPLEUR Y, 1998, CARBOHYDRATE MIMICS

[6] APPROACH TO OXETANE AND FURAN NUCLEOSIDES WITH AN ANOMERIC CARBON SUBSTITUENT - NUCLEOPHILIC-SUBSTITUTION AT HIGHLY HINDERED ALPHA-BROMO-OXETANE-CARBOXYLATES AND ALPHA-TETRAHYDROFURAN-CARBOXYLATES [J].

CHOI, S ;

WITTY, DR ;

FLEET, GWJ ;

MYERS, PL ;

STORER, R ;

WALLIS, CJ ;

WATKIN, D ;

PEARCE, L .

TETRAHEDRON LETTERS, 1991, 32 (29) :3569-3572

[7]

DESCOURS D, 1977, EUR J MED CHEM, V12, P313

[8] A GENERAL SYNTHETIC ROUTE TO ANOMERIC ALPHA-AZIDO AND ALPHA-AMINO-ACIDS AND FORMAL SYNTHESIS OF (+)-HIDANTOCIDIN [J].

DONDONI, A ;

SCHERRMANN, MC ;

MARRA, A ;

DELEPINE, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7517-7520

[9]

DUHAMEL P, 1970, B SOC CHIM FR, P3641

[10] SPIROCYCLIC PEPTIDES AT THE ANOMERIC POSITION OF MANNOFURANOSE [J].

ESTEVEZ, JC ;

ARDRON, H ;

WORMALD, MR ;

BROWN, D ;

FLEET, GWJ .

TETRAHEDRON LETTERS, 1994, 35 (47) :8889-8890

← 1 2 3 →