JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002478
Submitter
The Noguchi Institute
Reaction ID
R-0000-002478
Regist Date
2012/06/21 19:18:10
REACTANT
MOLECULE ID
JCGG-COM0003218 (Reaction Tree)
Mol
1 equiv.
MOLECULE ID
JCGG-COM0003213
Reactant Type
LiOOH
Mol
50 equiv.
MOLECULE ID
JCGG-COM0000649
Reactant Type
LiOH (1 M)
Mol
25 equiv.
MOLECULE ID
JCGG-COM0000418
Reactant Type
NaOH (2N)
Volume
1.0 mL
MOLECULE ID
JCGG-COM0000414
Reactant Type
H2 (gas)
MOLECULE ID
JCGG-COM0001026
Reactant Type
Pd/C (10%)
Mol
1 equiv.
MOLECULE ID
JCGG-COM0000552
Reactant Type
HCl (1N)
Volume
0.1 mL/5 mg
PRODUCT
MOLECULE ID
JCGG-COM0003219 (Reaction Tree)
Yield
52%
REACTION DETAIL
Reaction Time
16 hours, 18 hours, NOT specified
Reaction Temp
room temp, room temp, NOT specified
Solvent
THF (0.02M), MeOH, MeOH
Comment
1) 42+LiOOH, LiOH, 2) +NaOH, 3) +all the rest
NaOH was added until the pH of the solution reaches 14. (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

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