Efficient synthesis of α-C-galactosyl ceramide immunostimulants:: Use of ethylene-promoted olefin cross-metathesis

被引：69

作者：

Chen, GW

Schmieg, J

Tsuji, M

Franck, RW

机构：

[1] CUNY Hunter Coll, Dept Chem, New York, NY 10021 USA

[2] NYU, Sch Med, Dept Med & Mol Parasitol, New York, NY 10016 USA

[3] Rockefeller Univ, Aaron Diamond AIDS Res Ctr, New York, NY 10021 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 22期

关键词：

D O I：

10.1021/ol0482137

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Olefin cross-metathesis has been used to prepare alpha-C-galactosylceramide derivatives. The metathesis process merged vinyl and propenyl glycosides with vinyl derivatives of phytosphingosine. The use of ethylene enhanced the yield of the methathesis step.

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页码：4077 / 4080

页数：4

相关论文

共 40 条

[1] New approaches to olefin cross-metathesis [J].

Blackwell, HE ;

O'Leary, DJ ;

Chatterjee, AK ;

Washenfelder, RA ;

Bussmann, DA ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71

[2] SYNTHESIS OF DERIVATIVES OF MURAMIC ACID AND C-1 HOMOLOGATED ALPHA-D-GLUCOSE AS POTENTIAL INHIBITORS OF BACTERIAL TRANSGLYCOSYLASE [J].

BROOKS, G ;

EDWARDS, PD ;

HATTO, JDI ;

SMALE, TC ;

SOUTHGATE, R .

TETRAHEDRON, 1995, 51 (29) :7999-8014

[3]

Chen GW, 2002, CHEM-EUR J, V8, P2717, DOI 10.1002/1521-3765(20020617)8:12<2717::AID-CHEM2717>3.0.CO

[4]

2-P

[5] Glycolipids from sponges.: 13.: Clarhamnoside, the first rhamnosylated α-galactosylceramide from Agelas clathrodes.: Improving spectral strategies for glycoconjugate structure determination [J].

Costantino, V ;

Fattorusso, E ;

Imperatore, C ;

Mangoni, A .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1174-1179

[6] Enyne metathesis (enyne bond reorganization) [J].

Diver, ST ;

Giessert, AJ .

CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382

[7] Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling [J].

Dondoni, A ;

Mariotti, G ;

Marra, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4475-4486

[8] A concise C-glycosyl amino acid synthesis by alkenyl C-glycoside-vinyloxazolidine cross-metathesis.: Synthesis of glycosyl serine, asparagine and hydroxynorvaline isosteres [J].

Dondoni, A ;

Giovannini, PP ;

Marra, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (19) :2380-2388

[9] STEREOSELECTIVE SYNTHESIS OF ALPHA-C-ALLYL-GLYCOPYRANODISES [J].

GIANNIS, A ;

SANDHOFF, K .

TETRAHEDRON LETTERS, 1985, 26 (12) :1479-1482

[10] General access to iminosugar C-glycoside building blocks by means of cross-metathesis:: A gateway to glycoconjugate mimetics [J].

Godin, G ;

Compain, P ;

Martin, OR .

ORGANIC LETTERS, 2003, 5 (18) :3269-3272

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