JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001077
Submitter
The Noguchi Institute
Reaction ID
R-0000-001084
Regist Date
2012/06/21 16:38:20
REACTANT
MOLECULE ID
JCGG-COM0001209 (Reaction Tree)
Reactant Type
octasaccharide
Mol
0.0150 mmol
MOLECULE ID
JCGG-COM0000160
Reactant Type
Na (in 7 mL of liquid NH3)
Mol
2.43 mmol
MOLECULE ID
JCGG-COM0000500
Reactant Type
DMAP
Mol
catalytic amount
MOLECULE ID
JCGG-COM0000086
Reactant Type
Ac2O
Volume
0.3 mL
PRODUCT
MOLECULE ID
JCGG-COM0001210 (Reaction Tree)
Yield
43%
REACTION DETAIL
Reaction Time
45 minutes, overnight, 15 minutes, 18 hours
Reaction Temp
-78 degree C, room temp, room temp, room temp
Solvent
anhydrous THF, MeOH, MeOH, DMF/THF/Et3N = (1 mL of each)
Comment
1) Na+58, 2) +MeOH(solvent), 3) +Dowex 50-X8, 4) +all the rest
Dowex50-X8 was added at the start of the third phase.
COMMENT
There are four 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)