JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0001355
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-001355
Regist Date
 2012/06/21 16:53:05
REACTANT
MOLECULE ID
 JCGG-COM0001552 (Reaction Tree)
Skeleton
JCGG-STR032525
Mol
 7.65 mmol
MOLECULE ID
 JCGG-COM0000530
Reactant Type
 NaOMe
Mol
 0.765 mmol
MOLECULE ID
 JCGG-COM0000161
Reactant Type
 BnBr
Mol
 38.2 mmol
MOLECULE ID
 JCGG-COM0000160
Reactant Type
 NaH (60% in mineral oil)
Mol
 45.9 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0001553 (Reaction Tree)
Skeleton
JCGG-STR032525
Yield
 89%
REACTION DETAIL
Reaction Time
 1 hour, 15 minutes, 16 hours
Reaction Temp
 room temp, -30 degree C, room temp
Solvent
 MeOH, dry DMF, dry DMF
Comment
 1) 6a+NaOMe, 2) +BnBr, NaH, 3) temperature change
The solution from the first phase with BnBr was added to the solution of NaH in DMF over the reaction time. (second phase)
COMMENT
Keywords: carbohydrates, glycosides, glycosylation, oligosaccharides, thioimidates
There are multiple phases in this reaction.
ATTENTION: There is a numerical discrepancy between the scheme and the written method. (the number of % yield)
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)