A selective ring opening reaction of 4,6-O-benzylidene acetals in carbohydrates using trialkylsilane derivatives

Authors
Sakagami, M Hamana, H
Citation
M. Sakagami et H. Hamana, A selective ring opening reaction of 4,6-O-benzylidene acetals in carbohydrates using trialkylsilane derivatives, TETRAHEDR L, 41(29), 2000, pp. 5547-5551
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
29
Year of publication
2000
Pages
5547 - 5551
Database
ISI
SICI code
0040-4039(20000715)41:29<5547:ASRORO>2.0.ZU;2-O
Abstract
Reductive ring opening reactions of 4,6-O-benzylidene-protected carbohydrat es to the corresponding benzyl ethers using trialkylsilane derivatives were examined. When Et3SiH(or PS-DESTM)-TfOH was used, 6-O-benzyl ethers with 4 -hydroxy unsubstituted were obtained, while, when Et3SiH(or PS-DESTM)-PhBCl 2 was used, 4-O-benzyl ethers with 6-hydroxy unsubstituted were obtained in quantitative yield with excellent selectivity. (C) 2000 Elsevier Science L td. All rights reserved.