JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002471
Submitter
The Noguchi Institute
Reaction ID
R-0000-002471
Regist Date
2012/06/21 19:17:16
REACTANT
MOLECULE ID
JCGG-COM0003210 (Reaction Tree)
Mol
0.081 mmol
MOLECULE ID
JCGG-COM0000414
Reactant Type
H2 (gas)
MOLECULE ID
JCGG-COM0001026
Reactant Type
Pd/C (10%)
Weight
10 mg
MOLECULE ID
JCGG-COM0000552
Reactant Type
HCl (1 N)
Mol
catalytic amount
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Mol
0.484 mmol
MOLECULE ID
JCGG-COM0000783
Reactant Type
SnCl4
Mol
0.03 mmol
MOLECULE ID
JCGG-COM0000186
Reactant Type
TMSN3
Mol
0.06 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003211 (Reaction Tree)
Yield
61%
REACTION DETAIL
Reaction Time
2 days, overnight, 3 hours
Reaction Temp
room temp, NOT specified, room temp
Solvent
MeOH (5mL), pyridine (1mL), dry CH2Cl2 (6mL)
Comment
1) 36+H2, Pd/C, HCl, 2) +Ac2O, 3) +SnCl4, TMSN3
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)