JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002631
Submitter
The Noguchi Institute
Reaction ID
R-0000-002631
Regist Date
2012/06/21 19:33:01
REACTANT
MOLECULE ID
JCGG-COM0003422 (Reaction Tree)
Mol
14.2 mmol
MOLECULE ID
JCGG-COM0000830
Reactant Type
DBTO
Mol
14.2 mmol
MOLECULE ID
JCGG-COM0000660
Reactant Type
SOCl2 (in 10 mL of CH2Cl2)
Mol
14.2 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003423 (Reaction Tree)
Yield
86%
REACTION DETAIL
Reaction Time
6 hours, 1 hour
Reaction Temp
reflux, room temp
Solvent
dry MeOH (75mL), CH2Cl2 (100mL)
Comment
1) 15+DBTO, 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.
ATTENTION: There is a numerical discrepancy between the scheme and the written method. (the reaction time)
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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