74064-30-5

Upstream product

• 75212-02-1 (3S,5R)-3,5-Dihydroxy-2-methyl-cyclohex-1-enecarbaldehyde 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 35692-59-2 (1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 40983-58-2 methyl shikimate 
• 113261-67-9 C₉H₁₂O₅ 
• 121289-22-3 (4R,6S)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-1-iodomethyl-cyclohexene 
• 36616-60-1 (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 
• 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 
• 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 
• 74055-35-9 methyl (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-ene-1-carboxylate 

Downstream Products

• 74055-36-0 methyl (3S,5R)-3,5-bis-t-bytyldimethylsilyloxy-2-methylcyclohex-1-enecarboxylate 
• 116506-66-2 (3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(2,2-dibromo-vinyl)-2-methyl-cyclohexene 
• 116506-67-3 TB 
• 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 
• 74055-39-3 (3R,3aR,7aR)-7-{(E)-2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-vinyl}-3-((R)-1,5-dimethyl-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene 
• 108887-35-0 1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene 
• 41294-56-8 1α-hydroxyvitamin D3 
• 74055-38-2 Benzoic acid 1-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enyl]-2-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-2-(toluene-4-sulfonyl)-ethyl ester 

Relevant academic research and scientific papers

Synthesis of A-ring fragments of 1α,25-dihydroxyvitamin D3 and taxane diterpenoids: Effective construction of conjugated formylcyclohexene frameworks from isoxazolines

This paper have delineated the effectiveness of [3+2] cycloaddition process in the synthesis of multifunctional 6-membered rings. The novel synthesis of chiral A-ring fragment of 1α,25-dihydroxyvitamin D3 and also a novel route to A-ring fragme

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.

Efficient Enantiospecific Synthesis of Key A-Ring Synthons for the Preparation of 1α,25-Dihydroxyvitamin D3 Using a Chromium((II)-Mediated Reaction

Key A-ring synthons for the synthesis of 1α,25-dihydroxyvitamin D3 have been prepared efficiently from (R)-(-)-carvone by use of diastereoselective chromium(II)-mediated addition of an allylic halide to an aldehyde as a key step.

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.

STEREOSPECIFIC SYNTHESIS OF THE LYTHGOE'S RING A ALDEHYDE FOR THE PREPARATION OF 1α-HYDROXYLATED TACHYSTEROLS AND CALCIFEROLS

The dihydroxyaldehyde 1, an important intermediate for the synthesis of 1α-hydroxylated vitamin D derivatives via the corresponding tachysterol precursors, was prepared from (S)-(+)-carvone (6).The sequence involves as central step, the decarboxylation an

Calciferol and its Relatives. Part 27. A Synthesis of 1α-Hydroxyvitamin D3 by way of 1α-Hydroxytachysterol3

A new synthesis of 1α-hydroxyvitamin D3 is described.The bis-t-butyldimethylsilyl ether (17) of (3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-enecarbaldehyde and 8-p-tolylsulphonylmethyl-des-AB-cholest-8-ene (4) were combined to give mixed benzoyloxysulphones which, on reductive elimination with sodium amalgam, gave the corresponding bis-ether of 1α-hydroxytachysterol3.This was isomerised photochemically to the bis-ether of 1α-hydroxyprecalciferol3, and then thermally to give the bis-ether of 1α-hydroxyvitamin D3.Removal of protecting groups gave 1α-hydroxyvitamin D3 (21) in 62percent yield from the sulphone (4), or 12.8percent overall from cholesterol.