JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002894
Submitter
The Noguchi Institute
Reaction ID
R-0000-002894
Regist Date
2012/06/29 18:34:32
REACTANT
MOLECULE ID
JCGG-COM0002565 (Reaction Tree)
MOLECULE ID
JCGG-COM0004288 (Reaction Tree)
Reactant Type
(OBn, alpha-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-COM0004289 (Reaction Tree)
Product Type
alpha (OBn, alpha-OMe)
Yield
82%(alpha/beta=1/2.7)
MOLECULE ID
JCGG-COM0004290 (Reaction Tree)
Product Type
beta (OBn, alpha-OMe)
Yield
82%(alpha/beta=1/2.7)
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)