JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002456
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002456
Regist Date
 2012/06/21 19:15:48
REACTANT
MOLECULE ID
 JCGG-COM0003190 (Reaction Tree)
Skeleton
JCGG-STR008276
Mol
 1.66 mmol
MOLECULE ID
 JCGG-COM0000507
Reactant Type
 Et3SiH
Mol
 3.32 mmol
MOLECULE ID
 JCGG-COM0000099
Reactant Type
 BF3*Et2O
Mol
 4.98 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0003191 (Reaction Tree)
Skeleton
JCGG-STR008276
Yield
 73%
REACTION DETAIL
Reaction Time
 1 hour
Reaction Temp
 0 degree C
Solvent
 dry CH2Cl2 (20mL)
Comment
 The addition of Et3SiH was performed before the addition of BF3*Et2O.
COMMENT
Keywords: triazole, heparosan, chondroitin, copper catalyzed azide-alkyne cycloaddition, CuAAC, azido-glucuronic acid, glucosamine, galactosamine
ATTENTION: The chemical structure of 22 was drawn incorrectly. (bottom left of the scheme; OH in C-3 should be OBn)
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)