JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001353
Submitter
The Noguchi Institute
Reaction ID
R-0000-001353
Regist Date
2012/06/21 16:52:45
REACTANT
MOLECULE ID
JCGG-COM0001546 (Reaction Tree)
Reactant Type
donor
Mol
0.13 mmol
MOLECULE ID
JCGG-COM0001547 (Reaction Tree)
Reactant Type
acceptor
Mol
0.10 mmol
MOLECULE ID
JCGG-COM0000624
Reactant Type
AgOTf
Mol
0.26 mmol
MOLECULE ID
JCGG-COM0000047
Reactant Type
Et3N
Volume
0.5 mL
PRODUCT
MOLECULE ID
JCGG-COM0001548 (Reaction Tree)
Product Type
alpha
Yield
79%(alpha/beta=2.0/1)
MOLECULE ID
JCGG-COM0001549 (Reaction Tree)
Product Type
beta
Yield
79%(alpha/beta=2.0/1)
REACTION DETAIL
Reaction Time
16 hours, 30 minutes
Reaction Temp
room temp, NOT specified
Solvent
ClCH2CH2Cl, ClCH2CH2Cl
Comment
1) donor+acceptor, MS 3A, AgOTf, 2) +Et3N
The donor, the acceptor, and MS 3A were mixed and stirred for 1 hour before the reaction.
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 reaction time)
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

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