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Strategies for stereocontrol at C1 or C2 in syntheses of α‐glucosaminides
Author(s) -
FraserReid Bert,
Anilkumar G.,
Nair Latha G.,
Olsson Lars,
Martin Mercedes Garcia,
Daniels Jacquitta K.
Publication year - 2001
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/kdp7-d0ba-bn04-3h3a
Subject(s) - chemistry , stereocenter , nucleophile , hypervalent molecule , trifluoromethanesulfonate , azide , orthoester , stereochemistry , ring (chemistry) , coupling (piping) , asymmetric induction , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , mechanical engineering , reagent , engineering
The C1 and C2 stereocenters of α‐glucosaminides can be prepared by establishing the stereocenters in either order. For the former, a C2‐azido glucosyl donor is prepared first, and the restraining effect of a 4,6‐O‐benzylidene ring is used to induce α‐coupling. For the latter, the C1 linkage is prepared first by use of an n ‐pentenyl‐manno‐1,2‐orthoester donor which ensures (a) clean α‐coupling and (b) a convenient C2‐ester. The C2‐ester is replaced with a triflate leaving group, and nucleophilic displacement is effected by use of a hypervalent silicon azide.