JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002158
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002158
Regist Date
 2012/06/21 18:43:32
REACTANT
MOLECULE ID
 JCGG-COM0001260 (Reaction Tree)
Skeleton
JCGG-STR031569
Reactant Type
 glucose
Mol
 11.1 mmol
MOLECULE ID
 JCGG-COM0002803
Reactant Type
 MeHNOMe*HCl
Mol
 12.2 mmol
MOLECULE ID
 JCGG-COM0000398
Reactant Type
 NaOAc
Mol
 12.2 mmol
PRODUCT
MOLECULE ID
 JCGG-COM0002804 (Reaction Tree)
Yield
 92%
REACTION DETAIL
Reaction Time
 20 hours
Reaction Temp
 room temp
Solvent
 H2O
Comment
 The reactants were mixed at 0 degree in Celsius before stirred at room temperature.
COMMENT
Keywords: N,O-dimethyloxyamine-N-glycosides, protecting group manipulations, N-chlorosuccinimide, NCS, thioglycoside, trichloroacetimidate, complex oligosaccharide synthesis
REFERENCE
Reference Id
 REF-0000-000323
Issn
 Electronic
Doi
 10.1021/jo102372m
PubMed ID
 21332162
Journal Name
 The Journal of organic chemistry. (2011) 76 (6): 1918-21.
Article Title
 Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis.
Author
 Somnath, Dasgupta; Mark, Nitz
Affiliation
 Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, Canada M5S 3H6.
Reference Id
 REF-0000-000324
Source
 J. Org. Chem. 2011, 76, 1918-1921
Doi
 10.1021/jo102372m
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)