JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001366
Submitter
The Noguchi Institute
Reaction ID
R-0000-001366
Regist Date
2012/06/21 16:54:16
REACTANT
MOLECULE ID
JCGG-COM0001558 (Reaction Tree)
Reactant Type
donor
Mol
0.13 mmol
MOLECULE ID
JCGG-COM0001568 (Reaction Tree)
Skeleton
JCGG-STR032525
Reactant Type
acceptor
Mol
0.10 mmol
MOLECULE ID
JCGG-COM0000111
Reactant Type
TfOH
Mol
0.08 mmol
MOLECULE ID
JCGG-COM0000229
Reactant Type
Cu(OTf)2
Mol
0.26 mmol
MOLECULE ID
JCGG-COM0000047
Reactant Type
Et3N
Volume
0.5 mL
PRODUCT
MOLECULE ID
JCGG-COM0001569 (Reaction Tree)
Skeleton
JCGG-STR017858
Yield
80%
REACTION DETAIL
Reaction Time
NOT specified, 16 hours, 30 minutes
Reaction Temp
room temp, 40 degree C, NOT specified
Solvent
ClCH2CH2Cl, ClCH2CH2Cl, ClCH2CH2Cl
Comment
1) donor+acceptor, MS 4A, TfOH, 2) +Cu(OTf)2, 3) +Et3N
The donor, the acceptor, and MS 4A were mixed and stirred for 1 hour before the reaction.
The addition of Cu(OTf)2 (second phase initiation) was performed when donor was consumed.
COMMENT
Keywords: carbohydrates, glycosides, glycosylation, oligosaccharides, thioimidates
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000069
Issn
Print
Doi
10.1002/anie.200502694
PubMed ID
16224750
Journal Name
Angewandte Chemie (International ed. in English). (2005) 44 (43): 7123-6.
Article Title
Development of an arming participating group for stereoselective glycosylation and chemoselective oligosaccharide synthesis.
Author
James T, Smoot; Papapida, Pornsuriyasak; Alexei V, Demchenko
Affiliation
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
Reference Id
REF-0000-000070
Source
Angew. Chem. Int. Ed. 2005, 44, 7123-7126
Doi
10.1002/anie.200502694

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