JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001104
Submitter
The Noguchi Institute
Reaction ID
R-0000-001057
Regist Date
2012/06/21 16:36:57
REACTANT
MOLECULE ID
JCGG-COM0001165 (Reaction Tree)
Reactant Type
disilylglucal
Mol
4.26 mmol
MOLECULE ID
JCGG-COM0001172 (Reaction Tree)
Reactant Type
tribenzylfucosyl fluoride
Mol
4.26 mmol
MOLECULE ID
JCGG-COM0000032
Reactant Type
AgClO4
Mol
4.26 mmol
MOLECULE ID
JCGG-COM0000813
Reactant Type
SnCl2
Mol
4.26 mmol
MOLECULE ID
JCGG-COM0001173
Reactant Type
di-tert-butylpyridine
Mol
4.26 mmol
MOLECULE ID
JCGG-COM0000842
Reactant Type
K2CO3
Weight
0.8g
PRODUCT
MOLECULE ID
JCGG-COM0001167 (Reaction Tree)
Yield
64%
REACTION DETAIL
Reaction Time
22 hours, 20 hours
Reaction Temp
room temp, NOT specified
Solvent
Et2O, MeOH/THF = 2/1
Comment
1) 14+15, AgClO4, SnCl2, di-tert-butylpyridine, 2) +K2CO3
The reactants were mixed at 0 degree in Celsius, and allowed to raise to room temperature. (first phase)
MS 4A was included in the solvent. (first phase)
The reaction was conducted with exclusion of light. (first phase)
COMMENT
There are two phases in this reaction.
REFERENCE
Reference Id
REF-0000-000048
Issn
Print
PubMed ID
11273599
Journal Name
Journal of the American Chemical Society. (2001) 123 (1): 35-48.
Article Title
Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method.
Author
H M, Kim; I J, Kim; S J, Danishefsky
Affiliation
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Ave., New York, New York 10021, USA.
Reference Id
REF-0000-000049
Source
J. Am. Chem. Soc. 2001, 123, 35-48
Doi
10.1021/ja0022730

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)