JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001365
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001365
Regist Date
 2012/06/21 16:54:08
REACTANT
MOLECULE ID
 JCGG-COM0001558 (Reaction Tree)
Reactant Type
 donor
Mol
 0.13 mmol
MOLECULE ID
 JCGG-COM0001460 (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-COM0001567 (Reaction Tree)
Skeleton
JCGG-STR004384
Yield
 82%
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)