66774-84-3

Usage

Uses

(εR,1R,3aR,4S,7aR)-Octahydro-4-hydroxy-α,α,ε,7a-tetramethyl-1H-indene-1-pentanol is an intermediate in synthesizing (1α,3β,9β)-Cholesta-5,7-diene-1,3,25-triol (C431410), which is a natural secondary steroid used to determine the signal transduction pathways for rapid and genomic responses to calcitriol discrimination between different agonist shapes.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 100928-07-2 8β-hydroxy-de-A,B-27-norcholestan-25-one 
• 145223-32-1 2-[(S)-1-((1R,3aR,4S,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-ethyl]-5-methyl-5-triethylsilanyloxy-hexanenitrile 
• 103095-16-5 <1R-<1α(R*),3aβ,4α,7aα>>-octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<5-<(tetrahydro-2H-pyran-2-yl)oxy>-1,5-dimethylhexyl>-7a-methyl-1H-indene 
• 146434-16-4 <1R-<1α(R^*),3aβ,4α,7aα>>-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester 
• 74-88-4 methyl iodide 
• 70550-66-2 <1R-<1β(R*),3aα,4β,7aβ>>-Octahydro-4-acetoxy-α,α,ε,7a-tetramethyl-1H-indene-1-pentanol 
• 33813-99-9 Grundmann's alcohol 
• 917-54-4 methyllithium 
• 135359-40-9 de-A,B-24-(methoxycarbonyl)-cholestan-8β-ol 
• 307953-25-9 8β-[(tert-butyldimethylsilyl)oxy]-de-A,B-cholestan-25-ol 
• 147725-63-1 (8β,20R)-8-[(tert-butyldimethylsilyl)oxy]des-A,B-pregnan-20-ol 
• 502687-74-3 des-A,B-8β-[(tert-butyldimethylsilyl)oxy]-16α-[(methylsulfonyl)oxy]-25-[(trimethylsilyl)oxy]cholestane 
• 131336-04-4 (2R,3R)-3-<(1R)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone 

Downstream Products

• 70550-73-1 (1R,3aR,7aR)-1-[(2R)-6-hydroxy-6-methylhept-2-yl]-7a-methyloctahydroinden-4-one 
• 32222-06-3 calcitriol 
• 144848-24-8 25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one 
• 249928-69-6 C₃₁H₅₀O₃(SiC₆H₁₄)3 
• 130759-99-8 (R)-1-[(1S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-2-[(1R,3aS,7aR)-1-[(R)-5-(tert-butyl-dimethyl-silanyloxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol 
• 130760-01-9 (1R,3S,5R)-5-{(E)-2-[(1R,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,5,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methylene-cyclohexane-1,3-diol 

Relevant academic research and scientific papers

Preparation method of activated vitamin D3 drug CD ring intermediate

The invention relates to a preparation method of an activated vitamin D3 drug CD ring intermediate. The preparation method comprises the following steps: carrying out iodine substitution on a diol derivative 2 to obtain a compound 3, carrying out hydroxyl reaction on the compound 3 to obtain a compound 4, carrying out Michael addition reaction on the compound 4 to obtain a compound 5, carrying out nucleophilic addition reaction on the compound 5 to obtain a compound 6, carrying out deprotection reaction on the compound 6 to obtain a compound 7, and carrying out oxidation reaction on the compound 7 to obtain a compound 1, namely, the activated vitamin D3 drug CD ring intermediate (25-hydroxy Grundmann's one). The preparation method provided by the invention has the advantages that the steps are simple, the product yield is high, and massive 25-hydroxy Grundmann's one can be prepared.

VITAMIN D3 DERIVATIVES AND PHARMACEUTICAL USE THEREOF

The present invention relates to vitamin D3 derivatives of the following formula, wherein each symbol has the same meaning as defined herein, and pharmaceutical or medical use thereof for treating metabolic disease, liver disease, obesity, diabetes, cardiovascular disease, or cancer in a patient in need thereof.

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 of novel hapten derivatives of 1α,25-dihydroxyvitamin D3 and its 20-epi analogue

Hapten derivatives of 1α,25-dihydroxyvitamin D3 and its 20-epimer were synthesized and conjugated to a carrier protein for raising polyclonal antibodies. The haptens were linked through spacers at C-16, thereby exposing both the A-ring and the side chain of the molecules, to maximize antibody specificity. The spacers were introduced via stereoselective hydroboration of 16-ene intermediates as the key step. In immunoassays, the antibodies raised toward the natural hormone were selective to this compound over derivatives with modifications in the A-ring or the side chain. The antibodies toward the 20-epimer, however, were unable to recognize modifications in the side chain.

Synthesis of vitamin D3 and calcitriol dimers as potential chemical inducers of vitamin D receptor dimerization

The design and synthesis of vitamin D3 dimers 2 and 3 and, 1α,25-dihydroxyvitamin D3 (calcitriol) dimers 4 and 5 are described. The dimers were designed with a view to doubly binding the vitamin D receptor (VDR) and inducing the receptor homodimerization. In the dimers the units are linked through the C-11 position in ring C by an alkyl side chain of six or 10 carbon atoms, far from the hydroxy groups responsible for the VDR binding. The linker is formed by olefin metathesis of an olefinic side chain at the C-11 position introduced by stereoselective cuprate addition. The syhthesis, which is both short and convergent, uses the Wittig-Horner approach to construct the vitamin D triene system and allows the preparation of dimers with a linker of modulated length with the purpose of optimizing the vitamin D3-VDR interaction.

An efficient synthesis of the 25-hydroxy Windaus-Grundmann ketone

A short and efficient synthesis of the 25-hydroxy Windaus-Grundmann ketone from the Inhoffen-Lythgoe diol is described (seven steps, 70% overall). The most relevant feature of the synthesis is the preparation of the Wittig reagent 3 from cheap and commerc

Design and synthesis of a 1α,25-dihydroxyvitamin D3 dimer as a potential chemical inducer of vitamin D receptor dimerization

(matrix presented) A dimer comprising two 1α,25-dihydroxyvitamin D3 units linked by an alkyl side chain at C-11 was synthesized with a view to the simultaneous binding of two vitamin D receptor (VDR) molecules and the consequent induction of VD

Selective oxidation of terminal isopropyl groups to tertiary alcohols by electrochemical methodology

Selective oxidation of terminal isopropyl groups to the corresponding tertiary alcohols by an electrochemical method is described. Under the conditions using the TI(TFA)3-hematoporphyrin-O2- cathode reduction system, several substrates such as cholesterol (1) and Grundmann's alcohol (3) gave the corresponding tertiary alcohols 2 and 4, respectively, in reasonable yield.

Stereoselective Synthesis of Cyclopentanones by Reductive Cleavage of 6-Oxonorbornane-2-carboxylates and Its Application to the Synthesis of 1α,25-Dihydroxyvitamin D3 CD Ring

A novel chiral synthesis of the CD-ring 2 of 1α,25-dihydroxyvitamin D3 (1a) is described.The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposit

A nitrile approach to the synthesis of the side chain of vitamin D metabolites and analogues

An efficient new method for the construction of vitamin D hydroxylated side chains is described which is based on the alkylation and opening of epoxides by the α-anions derived from nitriles 6 and 7.