JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002591
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002591
Regist Date
 2012/06/21 19:29:21
REACTANT
MOLECULE ID
 JCGG-COM0003365 (Reaction Tree)
Skeleton
JCGG-STR031569
Mol
 0.65 mmol
MOLECULE ID
 JCGG-COM0000530
Reactant Type
 NaOMe (in MeOH)
Mol
 several drops
MOLECULE ID
 JCGG-COM0002419
Reactant Type
 TrtCl
Mol
 1.3 mmol
MOLECULE ID
 JCGG-COM0000847
Reactant Type
 DABCO
Mol
 1.3 mmol
MOLECULE ID
 JCGG-COM0000086
Reactant Type
 Ac2O
Mol
 5.2 mmol
MOLECULE ID
 JCGG-COM0000500
Reactant Type
 DMAP
Mol
 catalytic amount
PRODUCT
MOLECULE ID
 JCGG-COM0003366 (Reaction Tree)
Skeleton
JCGG-STR031569
Yield
 75%
REACTION DETAIL
Reaction Time
 3 hours, 24 hours, 5 hours
Reaction Temp
 room temp, room temp, NOT specified
Solvent
 anhydrous MeOH, dry CH2Cl2 (10.0mL), dry CH2Cl2 (10.0mL)
Comment
 1) 6+NaOMe, 2) +TrtCl, DABCO, 3) +Ac2O, DMAP
COMMENT
Keywords: 2-methylchromone-7-O-rutinosides, cytotoxicity, human tumor cell lines, acidic labile, 2-methylchromone aglycon
There are multiple phases in this reaction.
REFERENCE
Reference Id
 REF-0000-000355
Issn
 Electronic
Doi
 10.1021/jo102325s
PubMed ID
 21366286
Journal Name
 The Journal of organic chemistry. (2011) 76 (7): 2265-8.
Article Title
 Concise synthesis of 5-methoxy-6-hydroxy-2-methylchromone-7-O- and 5-hydroxy-2-methylchromone-7-O-rutinosides. Investigation of their cytotoxic activities against several human tumor cell lines.
Author
 Baolin, Wu; Wenpeng, Zhang; Zhonghua, Li; Li, Gu; Xin, Wang; Peng George, Wang
Affiliation
 Department of Chemistry, The Ohio State University, 484 West 12th Avenue, Columbus, Ohio 43210, USA.
Reference Id
 REF-0000-000356
Source
 J. Org. Chem. 2011, 76, 2265-2268
Doi
 10.1021/jo102325s
©2008-2013 Research Center for Medical Glycoscience, National Institute of Advanced Industrial Science and Technology (AIST)