208658-85-9

Upstream product

• 58558-53-5 (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 
• 208714-04-9 C₁₆H₂₀O₃ 
• 208658-91-7 (E)-7-Benzyloxy-5-methylene-hept-2-en-1-ol 

Downstream Products

• 208714-06-1 (R)-4-(4-Benzyloxy-2-methylene-butyl)-2-(4-methoxy-phenyl)-[1,3]dioxane 
• 208658-93-9 (R)-7-Benzyloxy-5-methylene-heptane-1,3-diol 
• 208659-01-2 {2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethoxymethyl}-benzene 
• 208658-97-3 Benzoic acid (R)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methylene-heptyl ester 
• 208658-95-1 Benzoic acid (R)-7-benzyloxy-3-hydroxy-5-methylene-heptyl ester 
• 208659-00-1 (1R,5R)-3-[2-Benzyloxy-eth-(Z)-ylidene]-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol 
• 208658-99-5 (R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methylene-heptan-1-ol 
• 208658-83-7 (R)-7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methylene-heptanal 
• 208714-02-7 (1R,3R)-5-(2-Benzyloxy-ethylidene)-cyclohexane-1,3-diol 
• 139356-39-1 (1R,3R)-1,3-bis((tert-butyldimethyl)silanyloxy)-5-[2-(diphenylphosphinoyl)-ethylidene]cyclohexane 
• 139356-38-0 ((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) 
• 139356-37-9 [(3R,5R)-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidene]-ethanol 
• 359761-70-9 (Z,1S,2R,6R)-1-fluoro-4-[2-(diphenylphosphinyl)ethylidene]-2,6-bis(triisopropylsilyloxy)cyclohexane 
• 359761-69-6 (Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane 

Relevant academic research and scientific papers

Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma

1α,25-Dihydroxyvitamin D3 (1α,25-D3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1α,25-D3 are required. Among them, 22-oxa-1α,25-D3 and 19-nor-1α,25-D3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2α position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1α,25-D3 analog, synthesized via the highly regio- and stereo-selective ring opening 2α-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2α-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma.

Asymmetric synthesis of a key ring a synthon for 1α-hydroxy-19-nor vitamin D

A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19- nor A-ring synthon 3.

"Symmetry" in the synthesis of the A-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions

The combination of the regioselective propiolate-ene reaction, catalytic enantioselective epoxidation and catalytic enantioselective carbonyl-ene cyclization completes the synthesis of the A ring of the hybrid 19-nor-22-oxa D3 analogue (1), which shows the significant activity in transactivation.