Reaction:JCGG-RAC0002600

JCGG ID

JCGG-RAC0002600

Submitter

The Noguchi Institute

Reaction ID

R-0000-002600

Regist Date

2012/06/21 19:30:08

REACTANT

MOLECULE ID

JCGG-COM0003374 (Reaction Tree)

Skeleton

JCGG-STR031569

Mol

0.23 mmol

MOLECULE ID

JCGG-COM0000530

Reactant Type

NaOMe (1 M in MeOH)

Mol

several drops

MOLECULE ID

JCGG-COM0002419

Reactant Type

TrtCl

Mol

0.46 mmol

MOLECULE ID

JCGG-COM0000847

Reactant Type

DABCO

Mol

0.92 mmol

MOLECULE ID

JCGG-COM0000086

Reactant Type

Ac2O

Mol

2.3 mmol

MOLECULE ID

JCGG-COM0000500

Reactant Type

DMAP

Mol

catalytic amount

PRODUCT

MOLECULE ID

JCGG-COM0003376 (Reaction Tree)

Skeleton

JCGG-STR031569

Yield

86%

REACTION DETAIL

Reaction Time

2 hours, overnight, 3 hours, 1 hour

Reaction Temp

room temp, room temp, reflux, room temp

Solvent

anhydrous MeOH (6.0mL), dry CH2Cl2 (5.0mL), dry CH2Cl2 (5.0mL), dry CH2Cl2 (5.0mL)

Comment

1) 12+NaOMe, 2) +TrtCl, DABCO, 3) temperature change, 4) +Ac2O, DMAP

Ac2O was added dropwise. (fourth 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