cas 62020-09-1, METHYL METHANESULFONYLACETATE | Articles data ｜lookchem

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62020-09-1

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Synthesis of the 6-Methylencarboxylic Acid Derivatives of Testosterone and Progesterone
The methyl 6β-(phenylsulfonyl)acetate and methyl 6β-(methylsulfonyl)acetate derivatives 8 and 10, respectively, of testosterone and of progesterone (9 and 11, respectively) were synthesized by allylic alkylation of the corresponding ?-allylpalladium chloride complexes 3 and 4.Chromatographic separation of the reaction mixtures yields as main products 8a and 9a with S configuration at the new asymmetric center.By-products 8b and 9b have R configuration.The corresponding by-products were not found in reaction mixtures of 10 and 11.The by-products 9c and 11c with α-configuration at C-17 (isoprogesterone derivatives) were isolated from the corresponding reaction mixtures.Alkaline treatment of the main products leads to the 6-methylenecarboxylic acid derivatives as a result of elimination and saponification: 8a and 11a gave 16 and 17.Base-catalyzed elimination of 9a yields the α,β-unsaturated methyl ester 19.NMR spectroscopic investigations (NOE, NOESY) of 19 support the predicted E configuration.
Handschuh, Dieter,Voelter, Wolfgang
p. 1007 - 1016
(2007/10/02)

Synthesis and Polymerization of Alkyl α-(Alkylsulfonyl)acrylates
Contrary to the reports in the patent literature, the title compounds could not be synthesized via the Mannich reaction with alkyl α-(alkylsulfonyl)acetate RSO2CH2COOR' (R = R' = CH3 or other alkyl groups).A synthetic sequence which utilizes selenoxide el
Gipstein, E.,Willson, C. G.,Sachdev, H. S.
p. 1486 - 1489
(2007/10/02)

11,12 Secoprostaglandins. 3. 8 Alkylthio(sulfinyl and sulfonyl) 12 hydroxyalkanoic acids and related compounds
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Smith,Bicking,Gould,Lee,Robb,Kuehl Jr.,Mandel,Cragoe Jr.
p. 540 - 547
(2007/10/12)

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Chemical Properties

Appearance/Colour :crystalline powder
Melting Point: 62 °C
Boiling Point: 296.3 °C at 760 mmHg
Flash Point:133 °C
Density: 1.277 g/cm³
Storage Temp.:2-8°C
Vapor Pressure: 0.00145mmHg at 25°C
Refractive Index: 1.437
BRN: 2412782
PSA: 68.82000
LogP: 0.28480

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