JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0000661
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-000661
Regist Date
 2012/06/21 16:17:25
REACTANT
MOLECULE ID
 JCGG-COM0000745 (Reaction Tree)
Skeleton
JCGG-STR002337
Reactant Type
 tetraacetate-NANA methyl ester
Mol
 0.41 mmol
MOLECULE ID
 JCGG-COM0000746
Reactant Type
 1H-tetrazole
Mol
 1.71 mmol
MOLECULE ID
 JCGG-COM0000747
Reactant Type
 phosphorimidite
Mol
 0.94 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0000748 (Reaction Tree)
Skeleton
JCGG-STR002337
Yield
 67%
REACTION DETAIL
Reaction Time
 The addition of phosphorimidite in a dropwise fashion and the additional 5 to 10 minutes.
Solvent
 THF
Comment
 The reaction temperature could not be found. (considered to be room temp)
COMMENT
The formula of the phosphorimidite may be wrong.
A mixture of anomeric phosphites was also obtained. (7%, alpha/beta = 20/1)
REFERENCE
Reference Id
 REF-0000-000030
Issn
 Print
PubMed ID
 10813908
Journal Name
 The Journal of organic chemistry. (2000) 65 (1): 144-51.
Article Title
 A total synthesis of the methyl glycoside of ganglioside GM(1).
Author
 S K, Bhattacharya; S J, Danishefsky
Affiliation
 Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
Reference Id
 REF-0000-000031
Source
 J. Org. Chem., 2000, 65, 144-151
Doi
 10.1021/jo9912496
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)