JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
JCGG-RAC0002781
Submitter
The Noguchi Institute
Reaction ID
R-0000-002781
Regist Date
2012/06/21 19:47:52
REACTANT
MOLECULE ID
JCGG-COM0003631 (Reaction Tree)
Mol
1.58 mmol
MOLECULE ID
JCGG-COM0003027
Reactant Type
TEMPO
Mol
0.32 mmol
MOLECULE ID
JCGG-COM0003176
Reactant Type
BAIB
Mol
3.95 mmol
MOLECULE ID
JCGG-COM0001727
Reactant Type
MeI
Mol
4.74 mmol
MOLECULE ID
JCGG-COM0000842
Reactant Type
K2CO3
Mol
4.74 mmol
PRODUCT
MOLECULE ID
JCGG-COM0003635 (Reaction Tree)
Yield
91%
REACTION DETAIL
Reaction Time
1 hour, overnight
Reaction Temp
room temp, room temp
Solvent
EtOAc/H2O = 6mL/3mL, dry DMF (9mL)
Comment
1) 15b+TEMPO, BAIB, 2) +all the rest
The reactants were mixed at 0 degree in Celsius before stirred at room temperature. (first 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)