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Sulfonium Triflate Mediated Glycosidations of Aryl 2‐Azido‐2‐deoxy‐1‐thio‐ D ‐mannosides
Author(s) -
Litjens Remy E. J. N.,
van den Bos Leendert J.,
Codée Jeroen D. C.,
van den Berg Richard J. B. H. N.,
Overkleeft Herman S.,
van der Marel Gijsbert A.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400784
Subject(s) - chemistry , sulfonium , trifluoromethanesulfonate , stereoselectivity , aryl , piperidine , stereochemistry , medicinal chemistry , sulfoxide , cyclopropane , yield (engineering) , thio , organic chemistry , salt (chemistry) , ring (chemistry) , catalysis , alkyl , materials science , metallurgy
The effectiveness in terms of yield and stereoselectivity of (phenylsulfinyl)piperidine (BSP) 1b / trifluoromethanesulfonic anhydride (Tf 2 O) and diphenyl sulfoxide (DPS) 1c /Tf 2 O‐mediated glycosidations of 2‐azido‐3‐ O ‐benzyl‐4,6‐ O ‐benzylidene‐2‐deoxy‐ D ‐thiomannosides 2a/b is described. Application of the BSP/Tf 2 O 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/Tf 2 O 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)