Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives

被引：20

作者：

Bouchez, V ^{[1
]}

Stasik, I ^{[1
]}

Beaupere, D ^{[1
]}

Uzan, R ^{[1
]}

机构：

[1] UNIV PICARDIE,CHIM ORGAN LAB,F-80039 AMIENS,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1997年 / 300卷 / 02期

关键词：

pentono-1,4-lactones; thionyl chloride; thionyl bromide; dimethylformamide; regioselective halogenation; 5-chloro-5-deoxy-pentono-1,4-lactone; 5-bromo-5-deoxy-pentono-1,4-lactone;

D O I：

10.1016/S0008-6215(97)00044-X

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Treatment of unprotected D-ribono, D-arabinono and D-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%-95% yields. Under the same conditions, D-lyxono-1,4-lactone resulted in the 2-halogeno compounds. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：139 / 142

页数：4

相关论文

共 18 条

[1] SELECTIVE CHLORINATION OF PENTITOLS [J].

BENAZZA, M ;

BEAUPERE, D ;

UZAN, R ;

DEMAILLY, G .

CARBOHYDRATE RESEARCH, 1991, 218 :75-81

[2] REGIOSELECTIVE CHLORINATION STUDY OF UNPROTECTED PENTITOLS - SYNTHESES OF SOME 1,5-DICHLORO-1,5-DIDEOXYPENTITOL DERIVATIVES [J].

BENAZZA, M ;

MASSOUI, M ;

UZAN, R ;

DEMAILLY, G .

CARBOHYDRATE RESEARCH, 1995, 275 (02) :421-431

[3] INHIBITION OF ARABINOSE 5-PHOSPHATE ISOMERASE - AN APPROACH TO THE INHIBITION OF BACTERIAL LIPOPOLYSACCHARIDE BIOSYNTHESIS [J].

BIGHAM, EC ;

GRAGG, CE ;

HALL, WR ;

KELSEY, JE ;

MALLORY, WR ;

RICHARDSON, DC ;

BENEDICT, C ;

RAY, PH .

JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (06) :717-726

[4] REACTION OF ALDONIC ACIDS WITH HYDROGEN BROMIDE .7. PREPARATION OF SOME 2,6-DIDEOXYHEXOSES [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C ;

REFN, S .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (09) :740-744

[5] REACTION OF ALDONIC ACIDS WITH HYDROGEN BROMIDE .3. THE PREPARATION OF SOME BROMODEOXY-PENTONOLACTONES AND DIBROMODIDEOXY-PENTONOLACTONES [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

CARBOHYDRATE RESEARCH, 1981, 90 (01) :17-26

[6] REACTION OF ALDONIC ACIDS WITH HYDROGEN BROMIDE .2. THE PREPARATION OF SOME BROMODEOXY-HEXOSES AND DEOXY-HEXOSES FROM BROMODEOXYALDONIC ACIDS [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

CARBOHYDRATE RESEARCH, 1981, 90 (01) :7-16

[7] REACTION OF ALDONIC ACIDS WITH HYDROGEN BROMIDE .1. PREPARATION OF SOME BROMODEOXYALDONIC ACIDS [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

CARBOHYDRATE RESEARCH, 1979, 68 (02) :313-319

[8] ALPHA-AMINO POLYHYDROXY TETRONIC AND PENTONIC ACIDS FROM BROMODEOXYALDONOLACTONES .9. [J].

BOLS, M ;

LUNDT, I .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1988, 42 (02) :67-74

[9] ALPHA-AMINO OR BETA-AMINO POLYHYDROXY ACIDS FROM THE REACTION OF BROMODEOXYALDONOLACTONES WITH LIQUID-AMMONIA [J].

BOLS, M ;

LUNDT, I .

ACTA CHEMICA SCANDINAVICA, 1991, 45 (03) :280-284

[10]

COLLINS PM, 1987, CARBOHYDRATES, P81