JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002460
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002460
Regist Date
 2012/06/21 19:16:10
REACTANT
MOLECULE ID
 JCGG-COM0003195 (Reaction Tree)
Skeleton
JCGG-STR008276
Reactant Type
 (in 45 mL of CH2Cl2)
Mol
 0.284 mmol
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
Mol
 0.568 mmol
MOLECULE ID
 JCGG-COM0000979
Reactant Type
 pyridine (diluted with 1 mL of CH2Cl2)
Volume
 0.09 mL
MOLECULE ID
 JCGG-COM0001852
Reactant Type
 NaNO2
Mol
 2.84 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0003196 (Reaction Tree)
Skeleton
JCGG-STR008362
Yield
 40%
REACTION DETAIL
Reaction Time
 30 minutes, 1 hour
Reaction Temp
 -18 degree C, room temp
Solvent
 CH2Cl2 (10mL), DMF (12mL)
Comment
 1) 27+Tf2O, pyridine, 2) +NaNO2
Pyridine was added dropwise. (first phase)
The addition of 27 was performed after the addition of all the other reactants. (first 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)