JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0000665
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-000665
Regist Date
 2012/06/21 16:17:37
REACTANT
MOLECULE ID
 JCGG-COM0000750 (Reaction Tree)
Reactant Type
 pentasaccharide
Mol
 0.03 mmol
MOLECULE ID
 JCGG-COM0000753
Reactant Type
 DMDO
Mol
 0.045 mmol
MOLECULE ID
 JCGG-COM0000754
Reactant Type
 ZnCl2
Mol
 0.045 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0000755 (Reaction Tree)
Skeleton
JCGG-STR027917
Yield
 86%
REACTION DETAIL
Reaction Time
 20 minutes, 30 minutes, 30 minutes, 5 hours + 30 minutes
Reaction Temp
 0 degree C, 0 degree C, -78 degree C, room temp
Solvent
 CH2Cl2, CH2Cl2, MeOH/THF, MeOH/THF
Comment
 1) 14+MS 4A, 2) +DMDO, 3) +ZnCl2, 4) temperature change
COMMENT
There are four phases in this reaction.
ATTENTION: There are numerical discrepancies between the scheme and the written method. (the number of % yield)
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)