JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0000727
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-000727
Regist Date
 2012/06/21 16:20:37
REACTANT
MOLECULE ID
 JCGG-COM0000802 (Reaction Tree)
Reactant Type
 donor
Mol
 210 micro mole
MOLECULE ID
 JCGG-COM0000803 (Reaction Tree)
Skeleton
JCGG-STR031555
Reactant Type
 acceptor
Mol
 420 micro mole
MOLECULE ID
 JCGG-COM0000129
Reactant Type
 promoter
Mol
 420 micro mole (*3)
MOLECULE ID
 JCGG-COM0000111
Reactant Type
 promoter
Mol
 130 micro mole (*3)
PRODUCT
MOLECULE ID
 JCGG-COM0000804 (Reaction Tree)
Product Type
 (2to3) glycoside alpha
Yield
 44%
MOLECULE ID
 JCGG-COM0000805 (Reaction Tree)
Product Type
 (2to3) glycoside beta
Yield
 14%
MOLECULE ID
 JCGG-COM0000806 (Reaction Tree)
Product Type
 (2to4) glycoside
Yield
 8%
MOLECULE ID
 JCGG-COM0000807 (Reaction Tree)
Product Type
 2,3-ene of donor
Yield
 16%
REACTION DETAIL
Reaction Time
 168 hours
Reaction Temp
 -50 degree C
Solvent
 EtCN
Catalyst
 promoter
Comment
 The promoter was added three times. (0 hour, 120 hours, and 144 hours)
3 A molecular sieve was included in the solvent.
COMMENT
REFERENCE
Reference Id
 REF-0000-000035
Issn
 Electronic
Doi
 10.1021/jo8027888
PubMed ID
 19296672
Journal Name
 The Journal of organic chemistry. (2009) 74 (8): 3009-23.
Article Title
 Ganglioside GQ1b: efficient total synthesis and the expansion to synthetic derivatives to elucidate its biological roles.
Author
 Akihiro, Imamura; Hiromune, Ando; Hideharu, Ishida; Makoto, Kiso
Affiliation
 Department of Applied Bioorganic Chemistry, Faculty of Applied Biological Sciences, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan. aimamura@ualberta.ca
Reference Id
 REF-0000-000036
Source
 J. Org. Chem. 2009, 74, 3009-3023
Doi
 10.1021/jo8027888
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)