JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002388
Submitter
The Noguchi Institute
Reaction ID
R-0000-002388
Regist Date
2012/06/21 19:08:35
REACTANT
MOLECULE ID
JCGG-COM0003107 (Reaction Tree)
Reactant Type
sugar
Mol
0.21 mmol
MOLECULE ID
JCGG-COM0000491
Reactant Type
AcOH (80% in H2O, solvent)
Volume
4.5 mL
MOLECULE ID
JCGG-COM0000759
Reactant Type
imidazole
Mol
0.526 mmol
MOLECULE ID
JCGG-COM0000939
Reactant Type
TBDPSCl
Mol
0.252 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003109 (Reaction Tree)
Yield
81%
REACTION DETAIL
Reaction Time
90 minutes, 10 minutes
Reaction Temp
85 degree C (reflux), room temp
Solvent
80% AcOH, CH3CN
Comment
1) sugar+AcOH, 2) +all the rest
COMMENT
Keywords: mannose, glucosamine, galactosamine, thioglycosides, 3-O-acylation, 4,6-O-benzylidenation, azide displacement, Lattrell-Dax inversion
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000337
Issn
Electronic
Doi
10.1021/jo200342v
PubMed ID
21510706
Journal Name
The Journal of organic chemistry. (2011) 76 (11): 4703-9.
Article Title
Rapid transformation of D-mannose into orthogonally protected D-glucosamine and D-galactosamine thioglycosides.
Author
Madhu, Emmadi; Suvarn S, Kulkarni
Affiliation
Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India.
Reference Id
REF-0000-000338
Source
J. Org. Chem. 2011, 76, 4703-4709
Doi
10.1021/jo200342v

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