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29838-67-3

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Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: Glycoside-flavonoid analogy
Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for SN1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles.
Ohmori, Ken,Hatakeyama, Keisuke,Ohrui, Hiroki,Suzuki, Keisuke
p. 1365 - 1373
(2007/10/03)

PROCESS FOR PREPARING FLAVONOIDS
A simple and easy process for preparing pharmacologically useful flavonoid compound having reductase inhibitory effect, active oxygen extinguishing effect, carcinogenesis promotion inhibitory effect, anti-inflammatory effect, and so on. Particularly, a process for preparing the compound of the formula (I): ???wherein, R2 is a substituted or un-substituted phenyl group; ???R7 is a hydrogen atom or a hydroxyl group; and n is an integer of 1 to 4; by bonding a sugar derivative to catechins as the starting compound selectively via O-glycoside bond and then oxidizing the 4-position of flavanoid skeleton of the obtained compound.
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Example 6

(2008/06/13)

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine
A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.
Ohmori, Ken,Ohrui, Hiroki,Suzuki, Keisuke
p. 5537 - 5541
(2007/10/03)

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Chemical Properties

Appearance/Colour :White powder
Melting Point: 180 °C (decomp)
Boiling Point: 801.1 °C at 760 mmHg
Flash Point:282.9 °C
Density: 1.74 g/cm³
Solubility:H2O: soluble1mg/mL, clear, colorless
Storage Temp.:2-8°C
Vapor Pressure: 4.42E-27mmHg at 25°C
Refractive Index: 1.748
PKA: 7.34±0.60(Predicted)
PSA: 186.37000
LogP: 0.03810

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