JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002319
Submitter
The Noguchi Institute
Reaction ID
R-0000-002319
Regist Date
2012/06/21 19:02:02
REACTANT
MOLECULE ID
JCGG-COM0003024 (Reaction Tree)
Mol
1.37 mmol
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Volume
7.8 mL
MOLECULE ID
JCGG-COM0000009
Reactant Type
TMSOTf
Mol
5.5 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003025 (Reaction Tree)
Yield
88%(at least)
REACTION DETAIL
Reaction Time
6 hours, 12 hours
Reaction Temp
-40 degree C, 0 to 4 degree C
Solvent
anhydrous CH2Cl2, anhydrous CH2Cl2
Comment
1) +all, 2) temperature change
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

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)