JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0000658
Submitter
The Noguchi Institute
Reaction ID
R-0000-000658
Regist Date
2012/06/21 16:17:17
REACTANT
MOLECULE ID
JCGG-COM0000734 (Reaction Tree)
Reactant Type
glycal
Mol
0.33 mmol
MOLECULE ID
JCGG-COM0000735
Reactant Type
benzenesulfonamide
Weight
52 mg
MOLECULE ID
JCGG-COM0000736
Reactant Type
IDCP
Mol
0.43 mmol
MOLECULE ID
JCGG-COM0000737
Reactant Type
LHMDS (1.0M in THF)
Volume
1 mL
MOLECULE ID
JCGG-COM0000738
Reactant Type
iodosulfonamide (in DMF)
Volume
3 mL
PRODUCT
MOLECULE ID
JCGG-COM0000739 (Reaction Tree)
Yield
40%
REACTION DETAIL
Reaction Time
10 minutes, 25 minutes, 1 hour, 1 hour
Reaction Temp
0 degree C, 0 degree C, -40 degree C, -10 degree C
Solvent
CH2Cl2, CH2Cl2, DMF, DMF
Comment
1) glycal+MS 4A, benzenesulfonamide, 2) +IDCP, 3) +LHDMS, iodosulfonamide, 4) temperature change
The glycal was azeotropically dried with anhydrous benzene and placed under vacuum overnight before the reaction.
MS 4A was included in the solvent. (first phase)
The reaction was conducted in dark condition. (second phase)
COMMENT
There are four phases in this reaction.
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)