JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001087
Submitter
The Noguchi Institute
Reaction ID
R-0000-001094
Regist Date
2012/06/21 16:38:50
REACTANT
MOLECULE ID
JCGG-COM0001224 (Reaction Tree)
Mol
0.181 mmol
MOLECULE ID
JCGG-COM0000500
Reactant Type
DMAP
Mol
catalytic amount
MOLECULE ID
JCGG-COM0000047
Reactant Type
Et3N
Mol
2.17 mmol
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Mol
2.17 mmol
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine
Volume
0.670 mL
MOLECULE ID
JCGG-COM0001177
Reactant Type
H2NNH2 (1 M in pyridine/AcOH=3/2)
Volume
0.670 mL
PRODUCT
MOLECULE ID
JCGG-COM0001226 (Reaction Tree)
Yield
73%(88%, 83%)
REACTION DETAIL
Reaction Time
40 hours, 4 hours
Reaction Temp
room temp, room temp
Solvent
CH2Cl2, CH2Cl2
Comment
1) 67+DMAP, Et3N, Ac2O, 2) +all the rest
The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (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)