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51863-60-6

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Synthesis of (R)-bambuterol based on asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with incubated whole cells of Williopsis californica JCM 3600
To achieve the synthesis of (R)-bambuterol, a prodrug of (R)-terbutaline, asymmetric reduction of 1-[3,5-bis(dimethylcarbamoyloxy)phenyl]-2-chloroethanone with whole cells of Williopsis californica JCM 3600 pre-incubated on glycerol as a carbon source was examined. Initially, the insolubility of this crystalline substrate (mp 126-127 C) in the incubation broth was an obstacle that needed to be overcome. To solve the problem, the concentration of glycerol was increased to 10% during reduction. Glycerol worked well for recycling oxido-reduction cofactors and for enhancing the water solubility of the substrate. The reduction proceeded smoothly to give enantiomerically pure (R)-alcohol in 81% isolated yield.
Asami, Kento,Machida, Takuya,Jung, Sonna,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
p. 106 - 109
(2013/10/01)

Microwave-assisted Deacetylation on Alumina: a Simple Deprotection Method
A simple high-yielding method for the deprotection of acetylated phenols and alcohols is described which occurs under mild conditions on an alumina surface using microwave irradiation.
Varma, Rajender S.,Varma, Manju,Chatterjee, Arnab K.
p. 999 - 1000
(2007/10/02)

A Practical Method for the Preparation of 2-Arylbenzofurans and the Synthesis of Moracin A and B
Oxidative rearrangement of 2-benzyloxychalcones 2 with Tl(NO3)3 in methanol to 1,2-diaryl-3,3-dimethoxy-1-propanones 3, alkaline degradation to aryl 2-benzyloxybenzyl ketones 4, debenzylation, and ring closure gave 2-arylbenzofurans 1.In this way moracin A and B (1a, b), further 2-(2,4-dihydroxyphenyl)-5,6-dimethoxybenzofuran (1c) were synthesized.The latter was not identical with a substance isolated from Myroxylon balsamum for which structure 1c was claimed.
Vu, Binh,Mezey-Vandor, Gabriella,Nogradi, Mihaly
p. 734 - 741
(2007/10/02)

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Chemical Properties

Appearance/Colour :White to off-white crystalline powder
Melting Point: 145-146 °C(lit.)
Boiling Point: 316.8 °C at 760 mmHg
Flash Point:159.6 °C
Density: 1.291 g/cm³
Solubility:DMSO (Slightly), Methanol (Slightly)
Storage Temp.:Inert atmosphere,Room Temperature
Refractive Index: 1.4447 (estimate)
PKA: 8.63±0.10(Predicted)
BRN: 1936502
PSA: 57.53000
LogP: 1.30040

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