JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002886
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002886
Regist Date
 2012/06/29 18:33:06
REACTANT
MOLECULE ID
 JCGG-COM0004270 (Reaction Tree)
Reactant Type
 n = 2
MOLECULE ID
 JCGG-COM0000043 (Reaction Tree)
Skeleton
JCGG-STR032526
Reactant Type
 ROH
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-COM0004271 (Reaction Tree)
Product Type
 alpha
Yield
 76%(alpha/beta=1/3.0)
MOLECULE ID
 JCGG-COM0004272 (Reaction Tree)
Product Type
 beta
Yield
 76%(alpha/beta=1/3.0)
REACTION DETAIL
Reaction Time
 NOT specified, NOT specified
Reaction Temp
 -60 degree C, NOT specified
Solvent
 CH2Cl2, NOT specified
Comment
 1) +all except ROH, 2) +ROH
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)