JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002571
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002571
Regist Date
 2012/06/21 19:27:39
REACTANT
MOLECULE ID
 JCGG-COM0003054 (Reaction Tree)
Skeleton
JCGG-STR032526
Reactant Type
 carbohydrate substrate
Mol
 1 equiv.
MOLECULE ID
 JCGG-COM0003328
Reactant Type
 R-X (alkyl halide)
Mol
 1.5 equiv.
MOLECULE ID
 JCGG-COM0003034 (Reaction Tree)
Reactant Type
 2-aminoethyl diphenylborinate
Mol
 10 mol %
MOLECULE ID
 JCGG-COM0001669
Reactant Type
 Ag2O
Mol
 1.1 equiv.
PRODUCT
MOLECULE ID
 JCGG-COM0003343 (Reaction Tree)
Skeleton
JCGG-STR032526
Yield
 90%
REACTION DETAIL
Reaction Time
 48 hours
Reaction Temp
 40 degree C
Solvent
 MeCN
COMMENT
Keywords: monoalkylations, regioselective, catalyst, cis-vicinal diol motifs, diphenylborinic ester precatalyst
REFERENCE
Reference Id
 REF-0000-000353
Issn
 Electronic
Doi
 10.1021/ol200990e
PubMed ID
 21591630
Journal Name
 Organic letters. (2011) 13 (12): 3090-3.
Article Title
 Regioselective alkylation of carbohydrate derivatives catalyzed by a diarylborinic acid derivative.
Author
 Lina, Chan; Mark S, Taylor
Affiliation
 Department of Chemistry, University of Toronto, 80 St. George Street, Toronto ON M5S 3H6, Canada.
Reference Id
 REF-0000-000354
Source
 Org. Lett., Vol. 13, No. 12, 2011
Doi
 10.1021/ol200990e
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)