JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001076
Submitter
The Noguchi Institute
Reaction ID
R-0000-001083
Regist Date
2012/06/21 16:38:16
REACTANT
MOLECULE ID
JCGG-COM0001208 (Reaction Tree)
Reactant Type
azeotropically dried hexasaccharide
Mol
0.0390 mmol
MOLECULE ID
JCGG-COM0001179 (Reaction Tree)
Reactant Type
fucosyl fluoride
Mol
0.196 mmol
MOLECULE ID
JCGG-COM0001173
Reactant Type
di-tert-butylpyridine
Mol
0.28 mmol
MOLECULE ID
JCGG-COM0000008
Reactant Type
Sn(OTf)2 (in 0.650 mL of THF)
Mol
0.137 mmol
PRODUCT
MOLECULE ID
JCGG-COM0001209 (Reaction Tree)
Yield
70%
REACTION DETAIL
Reaction Time
10 minutes, 24 hours
Reaction Temp
room temp, -7 degree C
Solvent
anhydrous PhCH3, anhydrous PhCH3
Comment
1) 57+23, MS 4A, di-tert-butylpyridine, 2) +Sn(OTf)2
MS 4A was included in the solvent.
The reactants were mixed at -15 degree in Celsius, and allowed to warm to -7 degree. (second 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)