JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002475
Submitter
The Noguchi Institute
Reaction ID
R-0000-002475
Regist Date
2012/06/21 19:17:46
REACTANT
MOLECULE ID
JCGG-COM0003206 (Reaction Tree)
Mol
0.077 mmol
MOLECULE ID
JCGG-COM0000426
Reactant Type
DIEA
Mol
1.54 mmol
MOLECULE ID
JCGG-COM0003209
Reactant Type
MOMCl
Mol
0.154 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003216 (Reaction Tree)
Yield
81%
REACTION DETAIL
Reaction Time
overnight
Reaction Temp
30 degree C
Solvent
dry CH2Cl2 (1mL)
Comment
The reactants were mixed at 0 degree in Celsius before stirred at 30 degree.
All the reactants except MOMCl were mixed before the cooling.
MOMCl was added dropwise.
COMMENT
Keywords: triazole, heparosan, chondroitin, copper catalyzed azide-alkyne cycloaddition, CuAAC, azido-glucuronic acid, glucosamine, galactosamine
ATTENTION: DMAP appearing in the scheme is not mentioned in the written method.
ATTENTION: There is a discrepancy between the scheme and the written method. (the reaction temperature)
REFERENCE
Reference Id
REF-0000-000343
Issn
Electronic
Doi
10.1021/jo200076z
PubMed ID
21438620
Journal Name
The Journal of organic chemistry. (2011) 76 (9): 3181-93.
Article Title
Design and synthesis of unnatural heparosan and chondroitin building blocks.
Author
Smritilekha, Bera; Robert J, Linhardt
Affiliation
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
Reference Id
REF-0000-000344
Source
J. Org. Chem. 2011, 76, 3181-3193
Doi
10.1021/jo200076z

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