JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0000666
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-000666
Regist Date
 2012/06/21 16:17:41
REACTANT
MOLECULE ID
 JCGG-COM0000755 (Reaction Tree)
Skeleton
JCGG-STR027917
Reactant Type
 methyl glycoside
Mol
 0.026 mmol
MOLECULE ID
 JCGG-COM0000412
Reactant Type
 TBAF (1M in THF)
Volume
 0.51 mL
MOLECULE ID
 JCGG-COM0000530
Reactant Type
 NaOMe (2% in MeOH)
Volume
 1 mL
MOLECULE ID
 JCGG-COM0000160
Reactant Type
 Na (ca. 4*4*4mm)
MOLECULE ID
 JCGG-COM0000756
Reactant Type
 NH3 (liquid)
Volume
 15 mL
MOLECULE ID
 JCGG-COM0000086
Reactant Type
 Ac2O
Volume
 2 mL
MOLECULE ID
 JCGG-COM0000531
Reactant Type
 H2O
Volume
 1 mL
PRODUCT
MOLECULE ID
 JCGG-COM0000757 (Reaction Tree)
Yield
 37%
REACTION DETAIL
Reaction Time
 48 hours, 48 hours, 24 hours, 30 minutes, 48 hours
Reaction Temp
 room temp, room temp, room temp, reflux of NH3, room temp
Solvent
 THF, THF/MeOH, THF/MeOH, THF/NH3, pyridine
Comment
 1) 16+TBAF, 2) +NaOMe, 3) +H2O, THF 4) +Dowex 50X8-400, NH3, Na, 5) +Dowex 50X8-400, Ac2O, pyridine
Dowex 50X8-400 was included in the solvent. (forth and fifth phases)
COMMENT
There are five phases in this reaction.
The solvent of the first phase may be wrong.
12% of the mixture of isomers was also 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)