145372-43-6

Usage

Uses

A novel 1,25-Dihydroxyvitamin D3 analog tested for vitamin D receptor binding affinity.

Upstream product

• 116535-65-0 (1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol 
• 1219444-01-5 (8E)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene-de-A,B-24(methoxycarbonyl)-cholestane 
• 191849-74-8 Trifluoro-methanesulfonic acid (2S,4R)-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methylene-hept-6-ynyl ester 
• 145372-41-4 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether 
• 145372-34-5 methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate 
• 145372-33-4 des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate 
• 145372-32-3 des-A,B-22-iodo-23,24-dinorcholan-8-one 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 74029-72-4 (5Z,7E)-(1S,3R)-1,3-dihydroxy-23a-homo-9,10-secochola-5,7,10⁽¹⁹⁾-trien-24-oic acid methyl ester 

Downstream Products

• 140710-96-9 (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol 
• 194232-09-2 (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexan-1-ol 
• 185099-80-3 (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexanal 
• 114694-09-6 PRI-1890 
• 128387-25-7 (R)-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-nonan-2-ol 
• 185099-82-5 (E)-(R)-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-non-3-en-2-ol 
• 185099-81-4 (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester 
• 194232-11-6 (1R,3aS,7aR)-1-((R)-5-Benzenesulfonyl-1-methyl-pentyl)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-indene 
• 194232-10-5 Toluene-4-sulfonic acid (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexyl ester 
• 194232-12-7 (R)-4-Benzenesulfonyl-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-nonan-2-ol 
• 32222-06-3 calcitriol 

Relevant academic research and scientific papers

An expeditious route to 1α,25-dihydroxyvitamin D3 and its analogues by an aqueous tandem palladium-catalyzed a-ring closure and suzuki coupling to the C/D unit

Chemical equation presented Daily vitamins: A mild, general, and highly stereoselective Pd0-catalyzed cascade to the triene system of the hoi mone 1α,25-dihydroxyvitamin D3 and six representative analogues is reported. The intramolecular cyclization of an enol-triflate (lower fragment) followed in situ by Suzuki Miyaura coupling with an alkenyl boronic ester (upper fragment, also efficiently prepared by Pd0-catalyzed coupling) in equimolar amounts under protic conditions is ideal for the preparation of small amounts of new vitamin D analogues for biological testing (see scheme).

Synthesis and in vitro evaluation of side chain-unsaturated analogs of 24a,24b-dihomo-1,25-dihydroxycholecalciferol

A synthesis and an in vitro evaluation of side chain-unsaturated analogs 3 and 4 of 24a, 24b-dihomo-1,25-dihydroxycholecalciferol (1) are described. Novel C(23a,24)-vitamin D synthons (sulfone 10 and aldehyde 11) were used for the synthesis of analog 4 and for the efficient preparation of the parent compound 1. The synthetic approach developed allows the use of easily available side chain fragments, such as oxirane 12 or Wittig reagent 15 for the preparation of compound 1 and analog 4, respectively. Introduction of a 24aE double bond results in a selective, 1000-fold increase in the binding affinity of analog 4 for the vitamin D receptor, compared to the affinity of 1, whereas the affinity of 4 for the vitamin D-binding protein and the activity in stimulating the differentiation of human promyelocytic leukemia HL-60 cells remained largely unchanged.

Ultrasonically Induced Conjugate Addition of Iodides to Electron-Deficient Olefins and Its Application to the Synthesis of Side-Chain Analogs of the Hormone 1α,25-Dihydroxyvitamin D3

A versatile method for the rapid construction of fragments related to the upper part of vitamin D3 from the Lythgoe-Inhoffen diol is described.The key feature of the strategy is a new zinc-copper-induced conjugate addition of iodo triflate 10a to electron-deficient olefins under sonochemical aqueous conditions.These fragments are rapidly and efficiently transformed via the dienyne convergent approach to several derivatives of the hormone 1α,25-(OH)2-D3 modified at C-25.