359761-67-4

Upstream product

• 359761-66-3 (2R,3R)-5-[2-(benzyloxy)ethyl]-2-fluoro-3-triisopropylsilyloxy-5-hexenal 
• 1020727-66-5 (2S,3R)-5-[2-(benzyloxy)ethyl]-2-fluoro-3-triisopropyloxy-5-hexen-1-ol 
• 208714-04-9 C₁₆H₂₀O₃ 
• 1020727-65-4 (4R,5S)-2-[2-(benzyloxy)ethyl]-5-fluoro-4,6-bis(triisopropylsilyloxy)-1-hexene 
• 208658-91-7 (E)-7-Benzyloxy-5-methylene-hept-2-en-1-ol 
• 208658-85-9 (2R,3R)-5-[2-(benzyloxy)ethyl]-2,3-epoxy-5-en-1-hexanol 
• 58558-53-5 (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 

Downstream Products

• 1020727-67-6 (Z,1S,2R,6R)-4-[2-(benzyloxy)ethylidene]-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane 
• 359761-68-5 (Z,3R,4S,5R)-2-[4-fluoro-3,5-bis(triisopropylsilyloxy)cyclohexylidene]ethanol 
• 359761-69-6 (Z,1S,2R,6R)-4-(2-chloroethylidene)-1-fluoro-2,6-bis(triisopropylsilyloxy)cyclohexane 
• 359761-70-9 (Z,1S,2R,6R)-1-fluoro-4-[2-(diphenylphosphinyl)ethylidene]-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.