Synthesis 2018; 50(03): 593-598
DOI: 10.1055/s-0036-1591515
paper
© Georg Thieme Verlag Stuttgart · New York

Glycosylation of Stannyl Ceramides Promoted by Modified Montmorillonite­ in Supercritical Carbon Dioxide

a  Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, Ciudad de México, C.P. 09340, México   Email: joseantonio.moralesserna@xanum.uam.mx
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b  School of Chemistry, University of Leeds, Leeds, West Yorkshire, LS2 9JT, UK
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c  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México, 04510, México
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c  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México, 04510, México
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c  Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Ciudad de México, 04510, México
,
Gustavo García de la Mora
d  Departamento de Química Orgánica, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, México
› Author Affiliations
The authors are very grateful for the economic support acquired from CONACyT (Institutional Links FONCICYT-275694), FERMIC S. A. de C.V. and PRODEP-SEP (DSA/103.5/16/10288). J.A.M.S. and B.N.N. acknowledge support from the Royal Society, British Council, Newton Fund and Newton Fellowship Alumni Program.
Further Information

Publication History

Received: 12 August 2017

Accepted after revision: 06 October 2017

Publication Date:
07 November 2017 (online)

Abstract

The direct glycosylation of ceramides in supercritical carbon dioxide (scCO2) successfully proceeded to produce β-glycolipids in high yield and with full stereoselectivity. The reaction is promoted by montmorillonite modified with a superacid (CF3SO3H). The value of this protocol was demonstrated in the efficient synthesis of isoglobotrihexosylceramide (iGB3).

Supporting Information

 
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