JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001074
Submitter
The Noguchi Institute
Reaction ID
R-0000-001081
Regist Date
2012/06/21 16:38:11
REACTANT
MOLECULE ID
JCGG-COM0001206 (Reaction Tree)
Reactant Type
hydroxy tetrasaccharide
Mol
0.0472 mmol
MOLECULE ID
JCGG-COM0001196 (Reaction Tree)
Reactant Type
thioglycoside
Mol
0.0943 mmol
MOLECULE ID
JCGG-COM0001173
Reactant Type
di-tert-butylpyridine
Mol
0.189 mmol
MOLECULE ID
JCGG-COM0000741
Reactant Type
MeOTf
Mol
0.377 mmol
PRODUCT
MOLECULE ID
JCGG-COM0001207 (Reaction Tree)
Yield
71%
REACTION DETAIL
Reaction Time
15 minutes, 24 hours
Reaction Temp
room temp, -40 degree C to room temp
Solvent
Et2O/CH2Cl2 = 3.4mL/1.7mL, Et2O/CH2Cl2 = 3.4mL/1.7mL
Comment
1) 55+47, MS 4A, di-tert-butylpyridine, 2) +MeOTf
MS 4A was included in the solvent.
The reactants were mixed at -40 degree in Celsius, and allowed to warm to room temperature slowly within the reaction time. (second phase)
COMMENT
There are two phases in this reaction.
There might be a typo in Supporting Info. (2,4-di-tert-butylpyridine should be 2,6-di-tert-butylpyridine)
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)