JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002709
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002709
Regist Date
 2012/06/21 19:41:04
REACTANT
MOLECULE ID
 JCGG-COM0003535 (Reaction Tree)
Reactant Type
 donor
Mol
 1 equiv.
MOLECULE ID
 JCGG-COM0003533 (Reaction Tree)
Reactant Type
 acceptor
Mol
 2 equiv.
MOLECULE ID
 JCGG-COM0003517
Reactant Type
 Ph2SO
Mol
 1.1 equiv.
MOLECULE ID
 JCGG-COM0002536
Reactant Type
 TTBP
Mol
 1.5 + 1.0 equiv.
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
Mol
 1.1 equiv.
PRODUCT
MOLECULE ID
 JCGG-COM0003536 (Reaction Tree)
Yield
 60%
REACTION DETAIL
Reaction Time
 30 minutes, NOT specified
Reaction Temp
 NOT specified, -60 degree C
Solvent
 CH2Cl2, CH2Cl2
Comment
 1) donor+Ph2SO, TTBP, MS 3A, 2) +Tf2O, acceptor, TTBP
MS 3A was included in the solvent.
The addition of Tf2O was performed before the addition of all the other reactants. (second phase)
Tf2O was added at -45 degree in Celsius, while all the other reactants were added at -60 degree. (second phase)
COMMENT
Keywords: Streptococcus pneumonia, SP1, zwitterionic polysaccharide, ZPs, cis-glycosidic bond
There are multiple phases in this reaction.
REFERENCE
Reference Id
 REF-0000-000363
Issn
 Electronic
Doi
 10.1021/jo102363d
PubMed ID
 21341806
Journal Name
 The Journal of organic chemistry. (2011) 76 (6): 1692-706.
Article Title
 Galacturonic acid lactones in the synthesis of all trisaccharide repeating units of the zwitterionic polysaccharide Sp1.
Author
 Alphert E, Christina; Leendert J, van den Bos; Herman S, Overkleeft; Gijsbert A, van der Marel; Jeroen D C, Codée
Affiliation
 Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Reference Id
 REF-0000-000364
Source
 J. Org. Chem. 2011, 76, 1692-1706
Doi
 10.1021/jo102363d
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)