JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002184
Submitter
The Noguchi Institute
Reaction ID
R-0000-002184
Regist Date
2012/06/21 18:45:27
REACTANT
MOLECULE ID
JCGG-COM0002827 (Reaction Tree)
Mol
0.11 mmol
MOLECULE ID
JCGG-COM0001547 (Reaction Tree)
Mol
0.10 mmol
MOLECULE ID
JCGG-COM0000229
Reactant Type
Cu(OTf)2
Mol
0.13 to 0.22 mmol
PRODUCT
MOLECULE ID
JCGG-COM0002828 (Reaction Tree)
Yield
89%
REACTION DETAIL
Reaction Time
3 hours
Reaction Temp
room temp
Solvent
(ClCH2)2
Comment
The donor, the acceptor, and molecular sieves (4 A) were mixed and stirred for 1 hour at room temperature before the reaction.
MS 4A was included in the solvent.
COMMENT
Keywords: S-thiazolinyl, STaz, S-benzoxazolyl, SBox, S-ethyl, anomeric leaving groups, activation, monosaccharide building blocks
REFERENCE
Reference Id
REF-0000-000325
Issn
Electronic
Doi
10.1021/jo201117s
PubMed ID
21797272
Journal Name
The Journal of organic chemistry. (2011) 76 (18): 7388-98.
Article Title
On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.
Author
Sophon, Kaeothip; Alexei V, Demchenko
Affiliation
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
Reference Id
REF-0000-000326
Source
J. Org. Chem. 2011, 76, 7388-7398
Doi
10.1021/jo201117s

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