3- /?-hydroxy-5a-pregnane-20-one

Cyano-3 -hydroxy-5a-pregnan-20-one A suspension of 5a-pregnane-3, 20-dione (2 g) in ethanol (90 ml) is treated with acetone cyanohydrin (4 ml) and three drops of triethylamine and stirred at room temperature until complete dissolution. After 3 hr, the solution is diluted with 200 ml of water, acidified with acetic acid and the crystalline precipitate is thoroughly washed with water and dried under vacuum to give 2.1 g (97%) of product mp 172-178° (dec). A sample recrystallized from ethyl acetate melts at 176-179° (dec) [a]p 86° (ethyl acetate). 

M-603) affords 1 la-hydroxy-17a-4-pr nene-3,20-dione. The thermodynamically more stable configuration of the side chain in pregnenolone and 3/3-hydroxy-5a-pregnan-20-one is the /3-form. If one makes the reasonable assumption that this... 

Hydroxypregna-5,16-dien-20-one, 134 3 -Hydroxypregna-5,16-dien-20-one acetate, 36, 196, 348, 349 3 -Hydroxypregna-5,16-dien-20-one acetate 20-ethyIene ketal, 210 3 -Hydroxypregna-5,16-dien-20-one acetate oxime, 143 3 -Hy droxy-5a-pregnan-20-one, 192 3p-Hydroxy-5a-pregnan-20-one 3-acetate, 264... 

Five 20-oxosteioids (pregnenolone, 3 -hydroxy-5a-, 3) -hydrpxy-5) -, 3a-hydropy-5a- and 3-hydroxy-5) -pregnan-20-one) and their sulfates were separated as their 4- A, Ar -dimethylaminosulfonyl)-7-hydrazino-2,l,3-benzoxadiazole derivatives on a Cjg column (A = 450nm, ex 550nm, em). The mobile phase was a 3/1 methanol/water (4mM y-cyclodextrin). Good resolution was obtained and elution was complete in 25 min [422],... 

The selective rearrangement of one epoxide ring to a ketone in vivo has been observed during metabolism of 5a,6a 16a,17a-diepoxy-3/S-hydroxy-5a-pregnan-20-one (433) by the fungus Curvularia lunata The previously... 

In the area of glycoslated steroids the a-L-rhamnosyl derivative of cholesterol has been made by a modified Lewis acid-catalysed route, and several standard syntheses of 17-glucosylated androstane and estradiol derivatives have been reported. Likewise, 3-p-hydroxy-5a-pregnan-20-one has been /3-glucosylated. ... 

A soln. of Na-methoxide in anhydrous methanol added to an anhydrous soln. of 17-(2 -carbomethoxyvinylidene)-5a-androstan-3/5-ol in methanol-methylene chloride, and allowed to stand 16 hrs. at room temp. -> 20-methoxy-21-carbomethoxy-5a-pregn-17(20)-en-3/ -ol (Y 95%) dissolved in methanol containing 18%-HCl, and left 5 hrs. at room temp. 2l-carbomethoxy-3/5-hydroxy-5a-pregnan-20-one (Y 97%). P. Crabbe et al., J. Org. Chem. 38, 1478 (1973). 

Preparation of 18,20-Cyclo-5a-pregnane-3, 20-diol 3-Acetate ° A solution of 5 g of 3j9-hydroxy-5oc-pregnan-20-one 3-acetate in 1000 ml of spectroscopically pure ethanol is irradiated with a 250 Watt Philips Biosol A mercury high pressure lamp No. 10/27 through a cental water cooled pyrex jacket under nitrogen for 4 hr. The solvent is then evaporated under reduced pressure and the residues from 2 such reactions are combined and chromatographed on 300 g of neutral alumina (activity II). 

Hydroxy-A-nor-5a,19 Cyclo-10a-androstan-3-one, 299 2 -Hydroxy-A-nor-5a-pregnan-20-one-2a-carboxylic acid, 422 3-Hydroxy-19-norpregna-l,3,5( 10)-triene-20-one, 173... 

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