JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0000663
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-000663
Regist Date
 2012/06/21 16:17:31
REACTANT
MOLECULE ID
 JCGG-COM0000752 (Reaction Tree)
Reactant Type
 diol
Weight
 260 mg
MOLECULE ID
 JCGG-COM0000748 (Reaction Tree)
Skeleton
JCGG-STR002337
Reactant Type
 phosphite
Mol
 0.355 mmol
MOLECULE ID
 JCGG-COM0000009
Reactant Type
 TMSOTf
Mol
 0.056 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0000749 (Reaction Tree)
Yield
 41%
REACTION DETAIL
Reaction Time
 30 minutes, 30 minutes, 55 minutes
Reaction Temp
 room temp, room temp, -40 degree C
Solvent
 CH3CN, CH3CN, CH3CN
Comment
 1) 9+MS 4A, 2) +13, 3) +TMSOTf
MS 4A was included in the solvent.
TMSOTf was added 15 minutes after the start of the third phase.
COMMENT
There are three phases in this reaction.
62% of total trisaccharide-product including byproducts was obtained.
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)