191677-71-1

Upstream product

• 54604-84-1 3β-hydroxy-5-α-androst-6-en-17-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 537674-07-0 3β-[(tert-butyldiphenylsilyl)oxy]-17,17-(ethylenedioxy)-androst-5-ene 
• 1609649-71-9 C₂₇H₃₆N₄ 
• 1526915-81-0 (3S,10R,13S,17S)-10,13-dimethyl-17-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 1526915-80-9 1-((3S,10R,13S,17S)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-4-phenyl-1H-1,2,3-triazole 
• 1526915-78-5 (((3S,10R,13S,17S)-17-azido-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)(tert-butyl)diphenylsilane 
• 939496-95-4 C₃₅H₄₆OSi 
• 1526915-76-3 (3S,10R,13S,17R)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-ol 
• 1526915-74-1 4-((3R,10R,13S,17R)-10,13-dimethyl-17-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)morpholine 
• 1526915-73-0 1-((3R,10R,13S,17R)-3-azido-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-4-phenyl-1H-1,2,3-triazole 
• 1526915-72-9 (3S,10R,13S,17R)-10,13-dimethyl-17-(4-phenyl-1H-1,2,3-triazol-1-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 
• 1526915-71-8 1-((3S,10R,13S,17R)-3-((tert-butyldiphenylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-4-phenyl-1H-1,2,3-triazole 
• 1526915-70-7 (((3S,10R,13S,17R)-17-azido-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)oxy)(tert-butyl)diphenylsilane 

Relevant academic research and scientific papers

CONTRACEPTIVE AGENTS

The invention provides compounds of formula I, II, III, or IV: wherein R1 to R11, X, and Y have any of the values defined in the specification. The compounds inhibit Na, K-ATPase α4 and are useful as contraceptive agents.

Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside

A facile synthetic approach toward six designed analogues (2-7) of linckoside B, a new neuritogenic steroid glycoside isolated from the Okinawan starfish Linckia laevigata, has been developed. The key steroid aglycon was achieved by a dimethylaluminum chloride-mediated 'ene' reaction. A versatile strategy was employed for the construction of glycosidic bonds through Schmidt's procedure using a glycosyl trichloroacetimidate donor.

NEUROSTEROID COMPOUNDS

The present invention relates to novel neurosteroid derivatives with anti-apoptotic, neuroprotective and neurogenic properties that act on the nervous system as well as methods for making the same and their applications in the treatment and/or prevention

Novel dehydroepiandrosterone derivatives with antiapoptotic, neuroprotective activity

DHEA analogues with modifications at positions C3 or C17 were synthesized and evaluated for neuroprotective activity against the neural-crest-derived PC12 cell model of serum deprivation-induced apoptosis. The most potent compounds were the spiro-epoxy de

Synthesis of xestobergsterol A from dehydroepiandrosterone

Xestobergsterol A, a potent inhibitor of histamine release, has been synthesized from dehydroepiandrosterone in a route that used introduction of a novel 15-oxygen functionality, side-chain construction via the orthoester Claisen rearrangement and TBAF-pr

Synthesis of a transmembrane ionophore based on a C2-symmetric polyhydroxysteroid derivative

The synthesis of the C2-symmetric bis-(20S)-5α-23,24-bisnorchol-16-en-3β,6α,7β-triol-22- terephthaloate (1), active as Na+-transporting transmembrane channel, has been achieved in 16 steps (10% overall yield) starting from the commercially available androst-5-en-3β-ol-17-one (3). The straightforward stereospecific functionalization of the side-chain, via the 'ene' reaction, and the successful regioselective terephthaloylation of the C-22 hydroxy group, illustrate the efficiency of the synthetic strategy.

A direct stereoselective synthesis of 7β-hydroxytestosterone

Although 7β-hydroxytestosterone is a known product of hepatic androgen metabolism, there are no published methods for its chemical synthesis except from the equally difficult to obtain 7β-hydroxy-4-androstene-3,17-dione. We found that several seemingly straightforward routes for its synthesis failed. Consequently, we tried to produce 7β-hydroxytestosterone by enzymatic oxidation of 5-androstene-3β,7β,17β-triol with cholesterol oxidase (Brevibacterium sp.), a procedure previously used to synthesize 7β-hydroxy- 4-cholesten-3-one from 3β,7β-dihydroxycholesterol (Alexander and Fisher 1995). However, 5-androstene-3β,7β,17β-triol was, at best, a very poor substrate for the enzyme leading to the production of 7β- hydroxytestosterone in only trace amounts. Thus, we explored a strategy for the enzymatic synthesis in which a C8-ester at C-17 (5-androstene- 3β,7β,17β-triol 17-caprylate) would serve to mimic the bulky and hydrophobic side chain of cholesterol and thus allow the C19-steroid to act as an effective substrate. When this ester was incubated with cholesterol oxidase, it was converted efficiently to 7β-hydroxytestosterone-17- caprylate. Attempts to remove the ester group by several mild hydrolytic procedures caused elimination of the 7β-hydroxyl group: we, therefore, obtained 7β-hydroxy-testosterone by incubation of the intermediate ester with porcine lipase.