JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002895
Submitter
The Noguchi Institute
Reaction ID
R-0000-002895
Regist Date
2012/06/29 18:34:44
REACTANT
MOLECULE ID
JCGG-COM0002565 (Reaction Tree)
MOLECULE ID
JCGG-COM0004291 (Reaction Tree)
Reactant Type
(OTDS, beta-OMe)
MOLECULE ID
JCGG-COM0002535
Reactant Type
BSP
MOLECULE ID
JCGG-COM0000761
Reactant Type
Tf2O
MOLECULE ID
JCGG-COM0002536
Reactant Type
TTBP
PRODUCT
MOLECULE ID
JCGG-COM0004292 (Reaction Tree)
Product Type
alpha (OTDS, beta-OMe)
Yield
80%(alpha/beta=1/2.2)
MOLECULE ID
JCGG-COM0004293 (Reaction Tree)
Product Type
beta (OTDS, beta-OMe)
Yield
80%(alpha/beta=1/2.2)
REACTION DETAIL
Reaction Time
NOT specified, NOT specified
Reaction Temp
-60 degree C, NOT specified
Solvent
CH2Cl2, NOT specified
Comment
1) +all except 73, 2) +73
Very few were described regarding this reaction.
COMMENT
Keywords: diastereoselective synthesis, critical interplay, 2-deoxy-beta-glycopyranosides, beta-mannopyranosides, alpha-sialosides, alpha-glucopyranosides, beta-arabinofuranosides
There are multiple phases in this reaction.
REFERENCE
Reference Id
REF-0000-000373
Issn
Electronic
Doi
10.1021/jo2017026
PubMed ID
21919522
Journal Name
The Journal of organic chemistry. (2011) 76 (22): 9193-209.
Article Title
Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.
Author
David, Crich
Affiliation
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA. dcrich@chem.wayne.edu
Reference Id
REF-0000-000374
Source
J. Org. Chem. 2011, 76, 9193-9209
Doi
10.1021/jo2017026

©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)