JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002386
Submitter
The Noguchi Institute
Reaction ID
R-0000-002386
Regist Date
2012/06/21 19:08:24
REACTANT
MOLECULE ID
JCGG-COM0003105 (Reaction Tree)
Mol
1.56 mmol
MOLECULE ID
JCGG-COM0000761
Reactant Type
Tf2O
Mol
3.12 mmol
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine
Mol
3.12 mmol
MOLECULE ID
JCGG-COM0000634
Reactant Type
NaN3
Mol
3.12 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003107 (Reaction Tree)
Yield
82%
REACTION DETAIL
Reaction Time
2 + 10 minutes, 1 hour
Reaction Temp
0 degree C, room temp
Solvent
CH2Cl2, DMF
Comment
1) +all except NaN3, 2) +NaN3
Tf2O was added dropwise.
Pyridine was added 2 minutes after the initiation of the reaction. (first phase)
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)