JCGGDB TOP Glycan Syntheses

Reaction

JCGG ID
 JCGG-RAC0002593
Submitter
 The Noguchi Institute
Reaction ID
 R-0000-002593
Regist Date
 2012/06/21 19:29:34
REACTANT
MOLECULE ID
 JCGG-COM0003367 (Reaction Tree)
Skeleton
JCGG-STR031569
Mol
 0.13 mmol
MOLECULE ID
 JCGG-COM0003368 (Reaction Tree)
Mol
 0.19 mmol
MOLECULE ID
 JCGG-COM0000009
Reactant Type
 TMSOTf
Mol
 1 + 1 equivalent
PRODUCT
MOLECULE ID
 JCGG-COM0003369 (Reaction Tree)
Skeleton
JCGG-STR007826
Yield
 60%
REACTION DETAIL
Reaction Time
 2 hours, 3 hours
Reaction Temp
 -20 to 0 degree C, 0 degree C
Solvent
 anhydrous CH2Cl2 (6.0mL), anhydrous CH2Cl2 (6.0mL)
Comment
 1) 8+9a, MS 4A, TMSOTf, 2) second addition of TMSOTf
MS 4A was included in the solvent.
8, 9a, and MS 4A were mixed and stirred for 1 hour at room temperature before the reaction.
The reactants were mixed at -20 degree in Celsius, and allowed to warm to 0 degree within the reaction time. (first phase)
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)