Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry

被引：29

作者：

Ali, Asghar ^{[1
]}

van den Berg, Richard J. B. H. N. ^{[1
]}

Overkleeft, Herman S. ^{[1
]}

Filippov, Dmitri V. ^{[1
]}

van der Marel, Gijsbert A. ^{[1
]}

Codee, Jeroen D. C. ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 19期

关键词：

SOLID-PHASE SYNTHESIS; OLIGOSACCHARIDE SYNTHESIS; SYNTHETIC PEPTIDES; ORGANIC-SYNTHESIS; PURIFICATION; TAG; GLYCOSYLATION; FRAGMENT; SUPPORT; SYSTEMS;

D O I：

10.1016/j.tetlet.2009.02.146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The methylsulfonylethoxycarbonyl (Msc) group is presented as a non-lipophilic, base-labile, participating protecting group for carbohydrate alcohols. It can be introduced using Msc-Cl and pyridine and is readily cleaved via beta-elimination under mild basic conditions. Its fluorous counterpart, the perfluorooctyl propyl-sulfonylethoxycarbonyl (FPsc) group, is used in a 'light fluorous' trisaccharide synthesis sequence. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2185 / 2188

页数：4

共 44 条

[1] THE 2-PHENYLSULFONYLETHYLCARBONYL (PSEC) GROUP FOR THE PROTECTION OF THE HYDROXYL FUNCTION [J].

BALGOBIN, N ;

JOSEPHSON, S ;

CHATTOPADHYAYA, JB .

TETRAHEDRON LETTERS, 1981, 22 (37) :3667-3670

[2] 2-(dimethyl (2-naphthylmethyl)silyl) ethoxy carbonate (NSEC) as a new mode of hydroxyl group protection [J].

Bufali, S ;

Hölemann, A ;

Seeberger, PH .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 2005, 24 (4-6) :441-462

[3] Oligosaccharide synthesis in microreactors [J].

Carrel, Frederic R. ;

Geyer, Karolin ;

Codee, Jeroen D. C. ;

Seeberger, Peter H. .

ORGANIC LETTERS, 2007, 9 (12) :2285-2288

[4] Chemoselective glycosylations using sulfonium triflate activator systems [J].

Codée, JDC ;

van den Bos, LJ ;

Litjens, REJN ;

Overkleeft, HS ;

van Boeckel, CAA ;

van Boom, JH ;

van der Marel, GA .

TETRAHEDRON, 2004, 60 (05) :1057-1064

[5] Ph2SO/Tf2O:: a powerful promotor system in chemoselective glycosylations using thioglycosides [J].

Codée, JDC ;

Litjens, REJN ;

den Heeten, R ;

Overkleeft, HS ;

van Boom, JH ;

van der Marel, GA .

ORGANIC LETTERS, 2003, 5 (09) :1519-1522

[6]

Crich D, 2001, SYNTHESIS-STUTTGART, P323

[7] Stereocontrolled glycoside and glycosyl ester synthesis.: Neighboring group participation and hydrogenolysis of 3-(2′-benzyloxyphenyl)-3,3-dimethylpropanoates [J].

Crich, David ;

Cai, Feng .

ORGANIC LETTERS, 2007, 9 (08) :1613-1615

[8] Preparation of a fluorous benzyl protecting group and its use in a fluorous synthesis approach to a disaccharide [J].

Curran, DP ;

Ferritto, R ;

Hua, Y .

TETRAHEDRON LETTERS, 1998, 39 (28) :4937-4940

[9] A novel, base-labile fluorous amine protecting group: synthesis and use as a tag in the purification of synthetic peptides [J].

de Visser, PC ;

van Helden, M ;

Filippov, DV ;

van der Marel, GA ;

Drijfhout, JW ;

van Boom, JH ;

Noort, D ;

Overkleeft, HS .

TETRAHEDRON LETTERS, 2003, 44 (50) :9013-9016

[10]

DINKELAAR J, J ORG CHEM UNPUB

← 1 2 3 4 5 →