JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002882
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002882
Regist Date
 2012/06/29 18:32:18
REACTANT
MOLECULE ID
 JCGG-COM0004259 (Reaction Tree)
MOLECULE ID
 JCGG-COM0004260 (Reaction Tree)
Skeleton
JCGG-STR031569
MOLECULE ID
 JCGG-COM0002535
Reactant Type
 BSP
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
MOLECULE ID
 JCGG-COM0002536
Reactant Type
 TTBP
MOLECULE ID
 JCGG-COM0000743
Reactant Type
 DDQ
PRODUCT
MOLECULE ID
 JCGG-COM0004261 (Reaction Tree)
Skeleton
JCGG-STR000114
Product Type
 alpha
Yield
 76.36%(alpha/beta=7/85)
MOLECULE ID
 JCGG-COM0004262 (Reaction Tree)
Skeleton
JCGG-STR027560
Product Type
 beta
Yield
 76.36%(alpha/beta=7/85)
REACTION DETAIL
Reaction Time
 NOT specified, NOT specified, NOT specified
Reaction Temp
 -78 degree C, NOT specified, NOT specified
Solvent
 CH2Cl2, NOT specified, NOT specified
Comment
 1) 35+BSP, Tf2O, TTBP, 2) +36, 3) +DDQ
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)