The synthesis of facial amphiphile 3α,7α-diaminocholestane
The facial amphiphile 3α,7α-diaminocholestane 3 was synthesized from 3β-acetoxy-7-ketocholestane 1 through a stepwise reductive amination. The reductive amination of 1 with NH4OAc in the presence of NaBH3CN, and protection with Boc2O yielded 7α-(tert-butyloxycarbonyl)-aminocholestane 4 in 86% yield. The reductive amination of 6, which was obtained from 4 after hydrolysis and subsequent oxidation, with NH4OTf in the presence of NaBH(OEh)3 provided 3 in 75% yield after protection with Boc2O.
Khan, Sharaf Nawaz,Cho, Nam-Ju,Kim, Hong-Seok
p. 5189 - 5192
(2008/02/08)
Synthesis and antifungal activity of oxygenated cholesterol derivatives
A series of oxygenated cholesterol derivatives were prepared from new synthetic methods and evaluated for their in vitro antimicrobial properties against human pathogens. The activity was highly dependent on the structure of the different compounds involved. The best results were obtained with hydroxy ketones 2, 4 and 5 and diketone 7 exhibiting activities against S. cerevisiae (ATCC 28383) and Candida albicans (CIP 1663-86). For example, compound 2 exhibited high activities against C. albicans (CIP 1663-86) and Amphotericine B and miconazole resistant strain C. albicans (CIP 1180-79) at a concentration of 1.5 μg/mL.
Brunel, Jean Michel,Loncle, Celine,Vidal, Nicolas,Dherbomez, Michel,Letourneux, Yves
p. 907 - 912
(2007/10/03)
Photoinduced Molecular Transformations. Part 136. Reactions of Alkoxyl Radicals generated from Hypoiodites of 3β-Hydroxy-7-oxo-Δ5-Steroids. Synthesis of Some Functionalized Oxasteroids
The synthesis of several unsaturated 3-oxasteroids and 4a-homo-4-oxasteroids of cholestane series functionalized at their B-ring is described; 3β-hydroxycholest-5-en-7-one and its 4,4-dimethyl derivative were transformed into 3-oxacholest-5-en-7-one and i
Suginome, Hiroshi,Kondoh, Takahiko
p. 3119 - 3124
(2007/10/02)
Functionalisation of Saturated Hydrocarbons. Part 6. Selective Oxidation of Steroids and Related Compounds
The oxidation of a series of steroids by the Gif system gives, almost without exception, the 20-ketone as major isolated product.The side-chain cleavage is made more selective by modification of rings A or B.The oxidation of oleana-1,12-diene-3,11-dione has also been studied and the two principal products have been identified.
Barton, Derek H. R.,Boivin, Jean,Hill, Christopher H.
p. 1797 - 1804
(2007/10/02)
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