JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002317
Submitter
The Noguchi Institute
Reaction ID
R-0000-002317
Regist Date
2012/06/21 19:01:50
REACTANT
MOLECULE ID
JCGG-COM0003021 (Reaction Tree)
Mol
0.268 mmol
MOLECULE ID
JCGG-COM0001026
Reactant Type
Pd/C (10%)
Weight
60 mg
MOLECULE ID
JCGG-COM0000414
Reactant Type
H2 (gas)
MOLECULE ID
JCGG-COM0000491
Reactant Type
AcOH
Volume
2 mL
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O (solvent)
Volume
0.5 mL
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine (solvent)
Volume
1 mL
PRODUCT
MOLECULE ID
JCGG-COM0003022 (Reaction Tree)
Yield
79%
REACTION DETAIL
Reaction Time
3 hours, overnight
Reaction Temp
room temp, room temp
Solvent
MeOH, Ac2O/pyridine
Comment
1) +all except Ac2O and pyridine 2) +Ac2O, pyridine
COMMENT
Keywords: 2-acylamino uronic acid, glycosyl phosphonates, oxidation, uronate 2-nitro-glycal, thermodynamic 1,2-trans-di-equatorial phosphonylation
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000331
Issn
Electronic
Doi
10.1021/jo2002193
PubMed ID
21495699
Journal Name
The Journal of organic chemistry. (2011) 76 (10): 4099-104.
Article Title
Accessing C-1 phosphonylated 2-acylamino uronic acids via 2-nitro-glycals.
Author
Beenu, Bhatt; Robin J, Thomson; Mark, von Itzstein
Affiliation
Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland 4222, Australia.
Reference Id
REF-0000-000332
Source
J. Org. Chem. 2011, 76, 4099-4104
Doi
10.1021/jo2002193

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