Sulfonium Triflate Mediated Glycosidations of Aryl 2-Azido-2-deoxy-1-thio-D-mannosides

Autor:	Gijsbert A. van der Marel, Jeroen D. C. Codée, Remy E. J. N. Litjens, Herman S. Overkleeft, Leendert J. van den Bos, Richard J. B. H. N. van den Berg
Rok vydání:	2005
Předmět:	Mannosides Sulfonium Aryl Trifluoromethanesulfonic anhydride Organic Chemistry Thio Medicinal chemistry chemistry.chemical_compound chemistry Organic chemistry Stereoselectivity Piperidine Physical and Theoretical Chemistry Trifluoromethanesulfonate
Zdroj:	European Journal of Organic Chemistry. 2005:918-924
ISSN:	1434-193X
DOI:	10.1002/ejoc.200400784
Popis:	The effectiveness in terms of yield and stereoselectivity of (phenylsulfinyl)piperidine (BSP) 1b/ trifluoromethanesulfonic anhydride (Tf2O) and diphenyl sulfoxide (DPS) 1c/Tf2O-mediated glycosidations of 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides 2a/b is described. Application of the BSP/Tf2O activator led to productive condensations using p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannoside (2b) as a donor, while the more powerful DPS/Tf2O combination gave similar results using both p-methoxyphenyl and phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides 2a/b. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
Databáze:	OpenAIRE
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