25095-07-2

Basic information

• Product Name: Acetic acid (2R,3S)-2-(3,4-dimethoxy-phenyl)-4,5,7-trimethoxy-chroman-3-yl ester
• CAS NO: 25095-07-2
• Molecular Weight: 418.444
• Mol File: 25095-07-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3S)-2-(3,4-dimethoxy-phenyl)-4,5,7-trimethoxy-chroman-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3S)-2-(3,4-dimethoxy-phenyl)-4,5,7-trimethoxy-chroman-3-yl ester(25095-07-2)
• EPA Substance Registry System: Acetic acid (2R,3S)-2-(3,4-dimethoxy-phenyl)-4,5,7-trimethoxy-chroman-3-yl ester(25095-07-2)

Safety Data

• Hazardous Substances Data: 25095-07-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 58065-35-3 (+)-catechin tetramethyl ether acetate 
• 58065-34-2 (-)-epicatechin tetramethyl ether 3-O-acetate 
• 108-24-7 acetic anhydride 
• 25095-06-1 (2R,3S)-2,3-trans-3',4,4',5,7-pentamethoxyflavan-3-ol 

Relevant articles and documents

Regio- and stereoselective oxidation of flavan-3-ol-, 4-arylflavan-3-ol-, and biflavanoid derivatives with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

The phenolic methyl esthers of flavan-3-ols, 4β-arylflavan-3-ols, and (-)-fisetinidol-(4β,8)-(+)-catechin biflavanoids are susceptible to regio- and stereoselective methoxylation at C-4 in moderate yields with DDQ in CHCl3-MeOH solution. The observed asymmetric induction with exclusive formation of 2,4-trans products is compatible with the intermediacy of a diastereogenic donor-acceptor interaction, DDQ acting as the acceptor and oxidant. The 4-funtionalized analogues are of both synthetic and degradative significance in condensed tannin chemistry.

Synthesis of Condensed Tannins. Part 1. Stereoselective and Stereospecific Syntheses of Optically Pure 4-Arylflavan-3-ols, and Assessment of their Absolute Stereochemistry at C-4 by means of Circular Dichroism

Stereoselective and also stereospecific condensation at C-4 of flavan-3,4-diols of known absolute configuration with phloroglucinol and resorcinol in acid medium proceeds at ambient temperatures with partial retention of configuration for 2,3-trans-isomers and with inversion for 2,3-cis-analogues.Circular dichroism spectra of the resultant 4-arylflavan-3-ols all exhibit multiple Cotton effects.The sign of high intensity Cotton effects to low wavelength, contributed by aryl chromophores at C-4, may almost invariably be correlated with the absolute configuration at this chiral centre of 2,3-trans-3,4-trans, 2,3-trans-3,4-cis, and 2,3-cis-3,4-trans-isomers.