140710-96-9

Usage

Uses

Used in Pharmaceutical Industry:
6-(4-2-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol is used as a potential pharmaceutical compound for its unique molecular structure and steric properties, which may offer advantages in drug design and development.
Used in Chemical Industry:
6-(4-2-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexylidene]-ethylidene-7a-methyl-octahydro-inden-1-yl)-2-methyl-heptan-2-ol is used as a chemical intermediate or reagent in various chemical synthesis processes, taking advantage of its specific functional groups and structural features.

InChI:InChI=1/C39H72O3Si2/c1-28(18-16-24-38(9,10)40)33-22-23-34-30(19-17-25-39(33,34)11)20-21-31-26-32(41-43(12,13)36(3,4)5)27-35(29(31)2)42-44(14,15)37(6,7)8/h20-21,28,32-35,40H,2,16-19,22-27H2,1,3-15H3/b30-20+,31-21+/t28-,32-,33-,34?,35+,39-/m1/s1

Upstream product

• 75-16-1 methylmagnesium bromide 
• 147125-21-1 ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(Z),7(E),10(19)-trien-25-oate 
• 143705-63-9 (E)-(20R)-de-A,B-8-(bromomethylene)cholestan-25-ol 
• 161055-41-0 (3S,5R)-3,5-bis(t-butyldimethylsilyloxy)octa-1-en-7-yne 
• 152032-72-9 (3S,5R)-3,5-dihydroxy-1-octen-7-yne 
• 203126-72-1 (3S,5R)-5-[(benzyloxymethyl)oxy]oct-1-en-7-yne-3-ol 
• 145372-41-4 1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether 
• 145372-32-3 des-A,B-22-iodo-23,24-dinorcholan-8-one 
• 116535-65-0 (1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 169900-32-7 ethyl (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate 
• 147125-06-2 (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 128387-35-9 (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 
• 170081-46-6 (6S)- and (6R)-SO₂ adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-9,10-secoergosta-5(E),7(E),10⁽¹⁹⁾,22(E)-tetraene 

Downstream Products

• 32222-06-3 calcitriol 

Relevant academic research and scientific papers

The synthesis of [26,27-11C]dihydroxyvitamin D3, a tracer for positron emission tomography (PET)

1α,25-Dihydroxyvitamin D3, an endogenous ligand with the highest affinity for the vitamin D receptor (VDR), was labeled with 11C for use in biological experiments. The radionuclide was incorporated via the reaction of [11C]methyllithium on a methyl ketone precursor in tetrahydrofuran at -10°C. Deprotection of the labeled intermediate yielded 2.5-3 GBq [26,27-11C]1α,25-dihydroxyvitamin D3 [11C-1,25(OH)2 D3] with specific radioactivity averaging 100 GBq/μmol at the end of synthesis and HPLC purification. The entire process took 48 min from the end of radionuclide production. In vitro binding experiments in rachitic chick purified VDR demonstrated the high affinity binding of this novel tracer. Thus; 11C-1,25(OH)2 D3 is available for in vivo distribution studies and may be suitable for the positron emission tomography (PET) determination of VDR levels and occupancy in animals and humans.

Efficient synthesis and biological evaluation of all A-ring diastereomers of 1α,25-dihydroxyvitamin D3 and its 20-epimer

An improved synthesis of the diastereomers of 1α,25-dihydroxyvitamin D3 (1) was accomplished utilizing our practical route to the A-ring synthon. We applied this procedure to synthesize for the first time all possible A- ring diastereomers of 20-epi-1α,25-dihydroxyvitamin D3 (2). Ten-step conversion of 1-(4-methoxyphenoxy)but-3-ene (6), including enantiomeric introduction of the C-3 hydroxyl group to the olefin by the Sharpless asymmetric dihydroxylation, provided all four possible stereoisomers of A- ring enynes (3), i.e., (3R,5R)-, (3R,5S)-, (3S,5R)- and (3S,5S)-bis[(tert- butyldimethylsilyl)oxy]oct-1-en-7-yne, in good overall yield. Palladium- catalyzed cross-coupling of the A-ring synthon with the 20-epi CD-ring portion (5), (E)-(20S)-de-A,B-8-(bromomethylene)cholestan-25-ol, followed by deprotection, afforded the requisite diastereomers of 20-epi-1α,25- dihydroxyvitamin D3 (2). The biological profiles of the synthesized stereoisomers were assessed in terms of affinities for vitamin D receptor (VDR) and vitamin D binding protein (DBP), HL-60 cell differentiation- inducing activity and in vivo calcium-regulating potency in comparison with the natural hormone. (C) 2000 Elsevier Science Ltd.

Nickel-Mediated Conjugate Addition. Elaboration of Calcitriol from Ergocalciferol

A convenient method for introduction the side chain of the hormone calcitriol (3) was achieved by coupling the nickel(0) complex derived from ethyl acrylate with the C-22 iodides 15, 16, 27, and 30 to give the corresponding esters 18, 21, 28, and 23 in yields of 73-82percent.Iodide 15 was also coupled with the Ni(0) complex derived from methyl vinyl ketone.The C-22 iodides 15 and 27 were obtained from ergocalciferol (6) and the 1(S),3(R)-bis-(5E,7E)-ergocalciferol derivative 24, respectively, by selective ozonolysis of their SO2 adducts, followed by in situ reduction of the ozonides with NaBH4 and iodination of the derived alcohols 14 and 26 with I2/PPh3/imidazole.The triene iodide 16 was prepared by extrusion of SO2 from 15, while 30 was obtained from the corresponding alcohol 29.Extrusion of SO2 from 21 and 28 gave the 5(E),7(E)-trienes 18 and 23, respectively.The latter was also made from the former by C-1 hydroxylation with selenium dioxide followed by silylation with tert-butyldimethylsilyl chloride and chromatographic separation.Completion of the synthesis of 3 was accomplished by treating 23 with methylmagnesium bromide to give 31, followed by desilylation with n-Bu4NF and triplet-sensitized photoisomerization.Alternatively, 31 was photoisomerized to 33, desilylation of which gave 3.Alcohol 33 was also prepared by the reaction of the 5Z,7E-triene ester 34, which was obtained by the photoisomerization of 23, with methylmagnesium bromide.

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.