JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002336
Submitter
The Noguchi Institute
Reaction ID
R-0000-002336
Regist Date
2012/06/21 19:03:29
REACTANT
MOLECULE ID
JCGG-COM0003043 (Reaction Tree)
Reactant Type
galactopyranose
Mol
3.15 mmol
MOLECULE ID
JCGG-COM0001646
Reactant Type
HBr (30% in AcOH)
Volume
2.3 mL
PRODUCT
MOLECULE ID
JCGG-COM0003044 (Reaction Tree)
Product Type
bromide
Yield
38%
REACTION DETAIL
Reaction Time
30 minutes + 1 hour, 2 hours
Reaction Temp
0 degree C, room temp
Solvent
CH2Cl2, CH2Cl2
Comment
1) +all, 2) temperature change
Preparation of Glycosyl Donors
HBr was added dropwise over 30 minutes.
COMMENT
Keywords: diphenylborinic acid, Koenigs-Knorr glycosylations, cis-1,2-diol, glycosyl halide donors, glycosidic linkages
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000333
Issn
Electronic
Doi
10.1021/ja2062715
PubMed ID
21838223
Journal Name
Journal of the American Chemical Society. (2011) 133 (35): 13926-9.
Article Title
Regioselective activation of glycosyl acceptors by a diarylborinic acid-derived catalyst.
Author
Christina, Gouliaras; Doris, Lee; Lina, Chan; Mark S, Taylor
Affiliation
Department of Chemistry, University of Toronto, Ontario, Canada.
Reference Id
REF-0000-000334
Source
J. Am. Chem. Soc. 2011, 133, 13926-13929
Doi
10.1021/ja2062715

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)