JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002616
Submitter
The Noguchi Institute
Reaction ID
R-0000-002616
Regist Date
2012/06/21 19:31:43
REACTANT
MOLECULE ID
JCGG-COM0003400 (Reaction Tree)
Reactant Type
intermediate 1
Mol
5.1 mmol
MOLECULE ID
JCGG-COM0003393
Reactant Type
N-Cbz-aminoethanol
Mol
10.2 mmol
MOLECULE ID
JCGG-COM0000009
Reactant Type
TMSOTf (1 N in CH2Cl2)
Volume
60 microL
PRODUCT
MOLECULE ID
JCGG-COM0003401 (Reaction Tree)
Product Type
intermediate 2 (beta)
Yield
55%
REACTION DETAIL
Reaction Time
2 hours
Reaction Temp
0 degree C
Solvent
dry CH2Cl2 (30mL)
Comment
All the reactants except TMSOTf were mixed and stirred for 15 minutes at room temperature before the reaction.
MS 4A was included in the solvent.
TMSOTf was added dropwise.
COMMENT
Keywords: Anthrose, Bacillus anthracis exosporium, antigenic determinants, fucose, cyclic sulfite, cyclic sulfate
REFERENCE
Reference Id
REF-0000-000359
Issn
Electronic
Doi
10.1021/jo200340q
PubMed ID
21678952
Journal Name
The Journal of organic chemistry. (2011) 76 (15): 5985-98.
Article Title
Access to antigens related to anthrose using pivotal cyclic sulfite/sulfate intermediates.
Author
Ophélie, Milhomme; Cédric, John; Florence, Djedaïni-Pilard; Cyrille, Grandjean
Affiliation
Laboratoire des Glucides, UMR CNRS 6219, Institut de Chimie de Picardie, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039 Amiens Cedex, France.
Reference Id
REF-0000-000360
Source
J. Org. Chem. 2011, 76, 5985-5998
Doi
10.1021/jo200340q

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