DIBUTYLSTANNYLENE ACETALS - USEFUL INTERMEDIATES FOR THE REGIOSELECTIVE SULFATION OF GLYCOSIDES

被引：55

作者：

GUILBERT, B ^{[1
]}

DAVIS, NJ ^{[1
]}

PEARCE, M ^{[1
]}

APLIN, RT ^{[1
]}

FLITSCH, SL ^{[1
]}

机构：

[1] DYSON PERRINS LAB,OXFORD OX1 3QY,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)86292-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Sulfated mono- and disaccharides were synthesised by a novel sulfation method via regioselective activation of the saccharides to their dibutyltin stannylene acetals, followed by treatment with sulfur trioxide-trimethylamine. This methodology was applied to the synthesis of 3'-sulfated lactosides 15 and 23, galactosylceramide sulfatide 3 and 2'-sulfated maltosides 30, 32 and 34.

引用

收藏

页码：2163 / 2178

页数：16

相关论文

共 32 条

[11] SIMPLE PROCEDURES FOR THE RAPID CLEAVAGE OF ESTER LIPIDS AND FOR THE LARGE-SCALE ISOLATION FROM BRAIN OF CEREBROSIDE SULFATE [J].

HARA, A ;

RADIN, NS .

ANALYTICAL BIOCHEMISTRY, 1979, 100 (02) :364-370

[12] 6'-SULFATED SIALYL-LEWIS-X IS A MAJOR CAPPING GROUP OF GLYCAM-1 [J].

HEMMERICH, S ;

ROSEN, SD .

BIOCHEMISTRY, 1994, 33 (16) :4830-4835

[13] Relations between rotatory power and structure in the sugar group. X.(2) The chloro-, bromo- and iodo-acetyl derivatives of lactose [J].

Hudson, CS ;

Kunz, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1925, 47 :2052-2055

[14] SYNTHETIC STUDIES TOWARD GANGLIOSIDES AND THEIR ANALOGS - SYNTHESIS OF APPROPRIATELY PROTECTED CORE OLIGOSACCHARIDES AS CONSTRUCTION BLOCKS [J].

KARTHA, KPR ;

KAMEYAMA, A ;

KISO, M ;

HASEGAWA, A .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (01) :145-158

[15] STUDIES ON THE 3-DIMENSIONAL BEHAVIOR OF THE SELECTIN LIGANDS LEWIS(A) AND SULFATED LEWIS(A) USING NMR-SPECTROSCOPY AND MOLECULAR-DYNAMICS SIMULATIONS [J].

KOGELBERG, H ;

RUTHERFORD, TJ .

GLYCOBIOLOGY, 1994, 4 (01) :49-57

[16] KINETICALLY CONTROLLED REGIOSPECIFIC SILYLATION OF POLYOLS VIA DIBUTYLSTANNANEDIYL ACETALS [J].

LEIGH, DA ;

MARTIN, RP ;

SMART, JP ;

TRUSCELLO, AM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) :1373-1374

[17]

LUCINEAU A, 1993, J CHEM SOC CHEM COMM, P1419

[18]

MACCARANA M, 1993, J BIOL CHEM, V268, P23898

[19] SELECTIVE FORMATION OF 2 ESTERS OF SOME METHYL ALPHA-DEUTERIUM-HEXOPYRANOSIDES VIA DIBUTYLSTANNYLENE DERIVATIVES [J].

MUNAVU, RM ;

SZMANT, HH .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (10) :1832-1836

[20]

NASHED MA, 1976, TETRAHEDRON LETT, V39, P3503

← 1 2 3 4 →