JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002617
Submitter
The Noguchi Institute
Reaction ID
R-0000-002617
Regist Date
2012/06/21 19:31:46
REACTANT
MOLECULE ID
JCGG-COM0003401 (Reaction Tree)
Reactant Type
intermediate 2 (beta)
Mol
2.8 mmol
MOLECULE ID
JCGG-COM0000530
Reactant Type
NaOMe (0.2 M in MeOH)
Mol
8.4 mmol
MOLECULE ID
JCGG-COM0000047
Reactant Type
TEA
Volume
1 mL
MOLECULE ID
JCGG-COM0000660
Reactant Type
SOCl2
Mol
3.6 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003395 (Reaction Tree)
Product Type
beta
Yield
87%
REACTION DETAIL
Reaction Time
1 hour, 2 hours
Reaction Temp
room temp, room temp
Solvent
MeOH (42mL), THF (10mL)
Comment
1) intermediate 2+NaOMe, 2) +all the rest
The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (second phase)
SOCl2 was added dropwise.
COMMENT
Keywords: Anthrose, Bacillus anthracis exosporium, antigenic determinants, fucose, cyclic sulfite, cyclic sulfate
There are multiple phases in this reaction.
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

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