JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002454
Submitter
The Noguchi Institute
Reaction ID
R-0000-002454
Regist Date
2012/06/21 19:15:39
REACTANT
MOLECULE ID
JCGG-COM0003189 (Reaction Tree)
Skeleton
JCGG-STR008276
Mol
4.57 mmol
MOLECULE ID
JCGG-COM0000530
Reactant Type
NaOMe (0.5 M in MeOH)
Mol
4.57 mmol
MOLECULE ID
JCGG-COM0000498
Reactant Type
p-TSA
Mol
0.096 mmol
MOLECULE ID
JCGG-COM0000375
Reactant Type
PhCH(OMe)2
Mol
4.81 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003188 (Reaction Tree)
Skeleton
JCGG-STR008276
Product Type
beta
Yield
81%
REACTION DETAIL
Reaction Time
3 hours, 12 hours
Reaction Temp
0 degree C, room temp
Solvent
dry MeOH (20mL), dry DMF (30mL)
Comment
1) 24+NaOMe, 2) +p-TSA, PhCH(OMe)2
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)