JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002788
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002788
Regist Date
 2012/06/21 19:48:56
REACTANT
MOLECULE ID
 JCGG-COM0003649 (Reaction Tree)
Reactant Type
 donor
Mol
 0.29 mmol
MOLECULE ID
 JCGG-COM0003650 (Reaction Tree)
Skeleton
JCGG-STR025316
Reactant Type
 acceptor
Mol
 0.39 mmol
MOLECULE ID
 JCGG-COM0003517
Reactant Type
 Ph2SO
Mol
 0.35 mmol
MOLECULE ID
 JCGG-COM0000761
Reactant Type
 Tf2O
Mol
 0.35 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0003651 (Reaction Tree)
Yield
 more than 98%
REACTION DETAIL
Reaction Time
 20 minutes, 15 minutes, 4 hours
Reaction Temp
 room temp, -60 degree C, -10 degree C
Solvent
 CH2Cl2 (5.8mL), CH2Cl2 (5.8mL), CH2Cl2 (5.8+2 mL)
Comment
 1) 41+Ph2SO, MS 3A, 2) +Tf2O, 3) +39
MS 3A was included in the solvent.
The reactants were mixed at -80 degree in Celsius before stirred at -60 degree. (second phase)
The reactants were mixed at -80 degree in Celsius before stirred at -10 degree. (third phase)
COMMENT
Keywords: mannuronic acids, mannopyranosides, mannopyranosyl methyl uronate, all-cis-linked tetrasaccharide
There are multiple phases in this reaction.
REFERENCE
Reference Id
 REF-0000-000367
Issn
 Electronic
Doi
 10.1021/jo201179p
PubMed ID
 21793528
Journal Name
 The Journal of organic chemistry. (2011) 76 (18): 7301-15.
Article Title
 Stereoselective synthesis of 2,3-diamino-2,3-dideoxy-β-D-mannopyranosyl uronates.
Author
 Marthe T C, Walvoort; Gert-Jan, Moggré; Gerrit, Lodder; Herman S, Overkleeft; Jeroen D C, Codée; Gijsbert A, van der Marel
Affiliation
 Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Reference Id
 REF-0000-000368
Source
 J. Org. Chem. 2011, 76, 7301-7315
Doi
 10.1021/jo201179p
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)