JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002773
Submitter
The Noguchi Institute
Reaction ID
R-0000-002773
Regist Date
2012/06/21 19:47:08
REACTANT
MOLECULE ID
JCGG-COM0003623 (Reaction Tree)
Mol
48.4 mmol
MOLECULE ID
JCGG-COM0000761
Reactant Type
Tf2O
Mol
112.5 mmol
MOLECULE ID
JCGG-COM0000979
Reactant Type
pyridine
Mol
1.13 mol
MOLECULE ID
JCGG-COM0000634
Reactant Type
NaN3
Mol
288 mmol
MOLECULE ID
JCGG-COM0001284
Reactant Type
NH4Cl
Mol
168 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003624 (Reaction Tree)
Yield
75%
REACTION DETAIL
Reaction Time
30 minutes, overnight
Reaction Temp
NOT specified, 80 degree C
Solvent
ClCH2CH2Cl (340mL), DMF (110mL)
Comment
1) 12+Tf2O, pyridine, 2) +all the rest
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)