116506-66-2

Upstream product

• 113375-50-1 (3S,5R)-5-Acetoxy-3-hydroxy-2-methylcyclohex-1-ene-1-carboxaldehyde 
• 113375-49-8 (1R,2S,4R,6S)-2-Hydroxymethyl-4-acetoxy-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 75212-02-1 (3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enecarbaldehyde 
• 113375-48-7 (1R,2S,4R,6S)-2-Hydroxymethyl-4-acetyl-1-methyl-7-oxabicyclo<4.1.0>heptane 
• 113375-47-6 (1R,2S,4R,6S)-2-Hydroxymethyl-1-methyl-4-(1-methylethenyl)-7-oxybicyclo<4.1.0>heptane 
• 4895-08-3 (1R,5R)-2-Methyl-5-(1-methylethenyl)-2-cyclohexen-1-methanol 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 
• 558-13-4 carbon tetrabromide 
• 74064-30-5 3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enecarbaldehyde 

Downstream Products

• 134328-87-3 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norvitamin D₃ tert-butyldimethylsilyl ether 
• 116572-09-9 1α-tert-Butyldimethylsilyloxy-6,7-dehydro-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether 
• 134328-86-2 1α-tert-Butyldimethylsilyloxy-25,25-(ethylenedioxy)-27-norprevitamin D₃ tert-butyldimethylsilyl ether 
• 77531-53-4 1α-Hydroxy-25-oxo-27-norvitamin D₃ 
• 32222-06-3 calcitriol 
• 116506-67-3 TB 

Relevant academic research and scientific papers

Palladium-catalysed coupling of vinyl triflates with enynes and its application to the synthesis of 1α,25-dihydroxyvitamin D3

We describe a general approach, based on the palladium-catalysed coupling of enynes with vinyl triflates, for the construction of dienynes related to vitamin D metabolites and analogues. As an application of this method, an efficient convergent synthesis of 1α,25-dihydroxyvitamin D3 starting from the Inhoffen-Lythgoe diol (6a) and natural carvones has been carried out (11 steps, 28% overall yield from 6a). This strategy allows labelling of the side chain in the final steps of the synthesis.

PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO 1α,25-DIHYDROXYVITAMIN D3

This note describes an efficient synthesis of a 25-functionalized dienyne precursor of the natural hormone 1α,25-dihydroxyvitamin D3 which allows easy labelling on the side chain.