A STEREOCONTROLLED CONSTRUCTION OF 2-DEOXY-BETA-GLYCOSIDIC LINKAGES VIA 1,2-TRANS-BETA-GLYCOSIDATION OF 2-DEOXY-2-[PARA-METHOXYPHENYL)THIO]GLYCOPYRANOSYL N,N,N',N'-TETRAMETHYLPHOSPHOROAMIDATES

被引：45

作者：

HASHIMOTO, S ^{[1
]}

YANAGIYA, Y ^{[1
]}

HONDA, T ^{[1
]}

IKEGAMI, S ^{[1
]}

机构：

[1] TEIKYO UNIV, FAC PHARMACEUT SCI, SAGAMIKO, KANAGAWA 19901, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 08期

关键词：

D O I：

10.1246/cl.1992.1511

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereocontrolled synthesis of 2-deoxy-beta-glycosides has been achieved by developing a salient 1,2-trans-glycosidation method with 2-deoxy-2-[(p-methoxyphenyl) thio]glycopyranosyl N,N,N',N'-tetramethylphosphoroamidates as glycosyl donors followed by a reductive removal of the p-methoxyphenylthio group with Raney nickel. The p-methoxyphenylthio group equatorially disposed at C-2 has proven to be an excellent stereodirecting auxiliary.

引用

页码：1511 / 1514

页数：4

共 37 条

[1] REDOX GLYCOSIDATION VIA THIONOESTER INTERMEDIATES [J].

BARRETT, AGM ;

BEZUIDENHOUDT, BCB ;

HOWELL, AR ;

LEE, AC ;

RUSSELL, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2275-2277

[2] 2-DEOXYGLYCOSYL PHOSPHORODITHIOATES - A NOVEL TYPE OF GLYCOSYL DONOR - EFFICIENT SYNTHESIS OF 2'-DEOXYDISACCHARIDES [J].

BIELAWSKA, H ;

MICHALSKA, M .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1991, 10 (01) :107-112

[3] PHOTOREMOVABLE HYDROXYL GROUP PROTECTION - USE OF THE PARA-TOLYSULFONYL PROTECTING GROUP IN BETA-DISACCHARIDE SYNTHESIS [J].

BINKLEY, RW ;

KOHOLIC, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (15) :3577-3581

[4] 2-BROMO-2-DEOXY SUGARS AS STARTING MATERIALS FOR THE SYNTHESIS OF ALPHA-GLYCOSIDE OR BETA-GLYCOSIDE OF 2-DEOXY SUGARS [J].

BOCK, K ;

LUNDT, I ;

PEDERSEN, C .

CARBOHYDRATE RESEARCH, 1984, 130 (JUL) :125-134

[5] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT [J].

BOLITT, V ;

MIOSKOWSKI, C ;

LEE, SG ;

FALCK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5812-5813

[6] DIASTEREOSELECTIVE FREE-RADICAL REACTIONS .1. PREPARATION OF 2-DEOXY-BETA-GLYCOSIDES BY SYNTHESIS AND REDUCTIVE DECARBOXYLATION OF 3-DEOXYULOSONIC ACID GLYCOSIDES [J].

CRICH, D ;

RITCHIE, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :945-954

[7] SILVER ZEOLITE AS PROMOTER IN GLYCOSIDE SYNTHESIS - THE SYNTHESIS OF 2-DEOXY-BETA-D-GLYCOPYRANOSIDES [J].

GAREGG, PJ ;

KOPPER, S ;

OSSOWSKI, P ;

THIEM, J .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (01) :59-65

[8] A STEREOSPECIFIC ROUTE TO 2-DEOXY-BETA-GLYCOSIDES [J].

GERVAY, J ;

DANISHEFSKY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5448-5451

[9] ARYLBIS(ARYLTHIO)SULFONIUM SALTS AS REAGENTS FOR THE SYNTHESIS OF 2-DEOXY-BETA-GLYCOSIDES [J].

GREWAL, G ;

KAILA, N ;

FRANCK, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2084-2092

[10] A RAPID AND EFFICIENT SYNTHESIS OF 1,2-TRANS-BETA-LINKED GLYCOSIDES VIA BENZYL-PROTECTED OR BENZOYL-PROTECTED GLYCOPYRANOSYL PHOSPHATES [J].

HASHIMOTO, S ;

HONDA, T ;

IKEGAMI, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :685-687

← 1 2 3 4 →