JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0001086
Submitter
The Noguchi Institute
Reaction ID
R-0000-001093
Regist Date
2012/06/21 16:38:46
REACTANT
MOLECULE ID
JCGG-COM0001194 (Reaction Tree)
Mol
1.19 mmol
MOLECULE ID
JCGG-COM0001174
Reactant Type
(Bu3Sn)2O
Mol
0.653 mmol
MOLECULE ID
JCGG-COM0001223 (Reaction Tree)
Mol
0.475 mmol
MOLECULE ID
JCGG-COM0001175
Reactant Type
AgBF4 (in 2 mL of THF)
Mol
1.25 mmol
PRODUCT
MOLECULE ID
JCGG-COM0001224 (Reaction Tree)
Yield
37%
MOLECULE ID
JCGG-COM0001225 (Reaction Tree)
Product Type
alpha-isomer
Yield
30%
REACTION DETAIL
Reaction Time
overnight, 15 minutes, 36 hours
Reaction Temp
reflux, room temp, 45 to 50 degree C
Solvent
anhydrous PhH, dry THF, dry THF
Comment
1) 43+(Bu3Sn)2O, 2) +66, MS 4A, 3) +AgBF4
MS 4A was included in the solvent.
COMMENT
There are three 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)