Glucuronidation of alcohols using the bromosugar-iodonium reagent method

被引：18

作者：

Stachulski, AV ^{[1
]}

机构：

[1] Ultrafine UFC Ltd, Manchester, Lancs, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 37期

关键词：

glucuronidation; iodine; pivaloate; bromosugars;

D O I：

10.1016/S0040-4039(01)01333-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The glycosidation method introduced by Field, employing bromosugars as donors in conjunction with iodine, has been evaluated for glucuronidation. Despite the low donor ability of glucuronates, beta -glucuronides were obtained in 70-85% yield from a number of primary alcohols, and in 50-65% from two secondary alcohols, using the pivaloyl compound 11 with NIS as promoter. By contrast, the use of IBr or ICI as promoter gave mainly the alpha -glucuronides. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6611 / 6613

页数：3

相关论文

共 17 条

[1]

Brown RT, 1997, J CHEM RES-S, P370

[2] SYNTHESIS OF A MORPHINE-6-GLUCURONIDE HAPTEN, N-(4-AMINOBUTYL)NORMORPHINE-6-GLUCURONID AND RELATED HAPTENS [J].

BROWN, RT ;

CARTER, NE ;

LUMBARD, KW ;

SCHEINMANN, F .

TETRAHEDRON LETTERS, 1995, 36 (47) :8661-8664

[3] Glucuronide and sulfate conjugates of ICI 182,780, a pure anti-estrogenic steroid. Order of addition, catalysis and substitution effects in glucuronidation [J].

Ferguson, JR ;

Harding, JR ;

Lumbard, KW ;

Scheinmann, F ;

Stachulski, AV .

TETRAHEDRON LETTERS, 2000, 41 (03) :389-392

[4] SYNTHESIS OF METHYL (ETHYL 2-O-ACYL-3,4-DI-O-BENZYL-1-THIO-BETA-D-GLUCOPYRANOSID)URONATES AND EVALUATION OF THEIR USE AS REACTIVE BETA-SELECTIVE GLUCURONIC-ACID DONORS [J].

GAREGG, PJ ;

OLSSON, L ;

OSCARSON, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2200-2204

[5] Iodine and its interhalogen compounds: versatile reagents in carbohydrate chemistry. XIV. Glycosylated amino acid synthesis [J].

Kartha, KPR ;

Ballell, L ;

Bilke, J ;

McNeil, M ;

Field, RA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (08) :770-772

[6]

Kartha KPR, 1996, TETRAHEDRON LETT, V37, P5175

[7] Iodine: A versatile reagent in carbohydrate chemistry .3. Efficient activation of glycosyl halides in combination with DDQ [J].

Kartha, KPR ;

Aloui, M ;

Field, RA .

TETRAHEDRON LETTERS, 1996, 37 (48) :8807-8810

[8]

MAYALARP SP, 1993, THESIS U MANCHESTER

[9] UTILITY OF GLYCOSYL PHOSPHITES AS GLYCOSYL DONORS - FRUCTOFURANOSYL AND 2-DEOXYHEXOPYRANOSYL PHOSPHITES IN GLYCOSIDE BOND FORMATION [J].

MULLER, T ;

SCHNEIDER, R ;

SCHMIDT, RR .

TETRAHEDRON LETTERS, 1994, 35 (27) :4763-4766

[10]

OSBORNE R, 1988, LANCET, V1, P828