JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002784
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002784
Regist Date
 2012/06/21 19:48:22
REACTANT
MOLECULE ID
 JCGG-COM0003641 (Reaction Tree)
Reactant Type
 donor
Mol
 1.04 mmol
MOLECULE ID
 JCGG-COM0003642
Reactant Type
 N-(benzyl)benzyloxycarbonyl-5-aminopentanol (acceptor)
Mol
 1.56 mmol
MOLECULE ID
 JCGG-COM0000111
Reactant Type
 TfOH
Mol
 0.21 mmol
MOLECULE ID
 JCGG-COM0000979
Reactant Type
 pyridine (solvent)
Volume
 6 mL
MOLECULE ID
 JCGG-COM0000086
Reactant Type
 Ac2O (solvent)
Volume
 2 mL
PRODUCT
MOLECULE ID
 JCGG-COM0003643 (Reaction Tree)
Skeleton
JCGG-STR025316
Product Type
 alpha
Yield
 95%(alpha/beta=7.4/1)
MOLECULE ID
 JCGG-COM0003644 (Reaction Tree)
Skeleton
JCGG-STR025230
Product Type
 beta
Yield
 95%(alpha/beta=7.4/1)
REACTION DETAIL
Reaction Time
 1 hour, 2 hours
Reaction Temp
 -10 degree C, room temp
Solvent
 Et2O (21mL), pyridine/Ac2O
Comment
 1) donor+acceptor, MS, TfOH, 2) +all the rest
Activated molecular sieves were included in the solvent.
The donor, the acceptor, and molecular sieves were mixed and stirred for 30 minutes at room temperature before the reaction.
The reactants were mixed at -40 degree in Celsius before stirred at -10 degree. (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)