JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002897
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002897
Regist Date
 2012/06/29 18:35:06
REACTANT
MOLECULE ID
 JCGG-COM0004295 (Reaction Tree)
MOLECULE ID
 JCGG-COM0004296 (Reaction Tree)
MOLECULE ID
 JCGG-COM0001846 (Reaction Tree)
Skeleton
JCGG-STR031569
MOLECULE ID
 JCGG-COM0000129
Reactant Type
 NIS
MOLECULE ID
 JCGG-COM0000111
Reactant Type
 TfOH
PRODUCT
MOLECULE ID
 JCGG-COM0004297 (Reaction Tree)
Yield
 55%
REACTION DETAIL
Reaction Time
 NOT specified, NOT specified
Reaction Temp
 -78 degree C, -78 degree C
Solvent
 CH2Cl2/CH3CN = 2/1, CH2Cl2/CH3CN = 2/1
Comment
 1) 87+88, NIS, TfOH, 2) +89, NIS, TfOH
Very few were described regarding this reaction.
Acid-washed MS was included in the solvent.
NIS and TfOH were added twice.
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)