Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions

Citation
V. Ferrieres et al., Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions, TETRAHEDR L, 41(29), 2000, pp. 5515-5519
Citations number
16
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
5515 - 5519
Database
ISI
SICI code
0040-4039(20000715)41:29<5515:SACOSG>2.0.ZU;2-Z
Abstract
Sulfinyl beta-D-galactofuranosides 3(R,S) and 9(R,S) were used as new hexof uranosyl donors in glycosylation reactions. Activation by trifluoromethanes ulfonic anhydride involved different reaction pathways depending on the ste reochemistry at the sulfur atom. Experimental results underlined a more sui table reactivity of 3(R) and 9(R) versus 3(S) and 9(S), respectively, for t he synthesis of beta-D-galactofuranosides. (C) 2000 Elsevier Science Ltd. A ll rights reserved.