JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002448
Submitter
The Noguchi Institute
Reaction ID
R-0000-002448
Regist Date
2012/06/21 19:15:09
REACTANT
MOLECULE ID
JCGG-COM0003181 (Reaction Tree)
Mol
2.19 mmol
MOLECULE ID
JCGG-COM0003027
Reactant Type
TEMPO
Mol
1.09 mmol
MOLECULE ID
JCGG-COM0003176
Reactant Type
BAIB
Mol
5.49 mmol
MOLECULE ID
JCGG-COM0000367
Reactant Type
Cs2CO3
Mol
7.67 mmol
MOLECULE ID
JCGG-COM0001727
Reactant Type
MeI
Mol
2.86 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003182 (Reaction Tree)
Yield
88%
REACTION DETAIL
Reaction Time
NOT specified, 1 hour
Reaction Temp
room temp, 0 degree C
Solvent
CH2Cl2/H2O = 15mL/5mL, DMF (25mL)
Comment
1) 16+TEMPO, BAIB, 2) +Cs2CO3, MeI
The addition of Cs2CO3 was performed before the reaction mixture was cooled to 0 degree in Celsius. (second phase)
COMMENT
Keywords: triazole, heparosan, chondroitin, copper catalyzed azide-alkyne cycloaddition, CuAAC, azido-glucuronic acid, glucosamine, galactosamine
There are multiple phases in this reaction.
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)