70550-73-1

Usage

Uses

Used in Pharmaceutical Development:
(1R,3aR,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one is used as a potential pharmaceutical candidate for [application reason] due to its unique structure and the presence of a hydroxyl group and chiral center, which may contribute to its biological activity.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (1R,3aR,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one serves as a valuable building block for the synthesis of other compounds with potential therapeutic applications. Its complex structure and functional groups offer opportunities for further chemical modifications and exploration of its properties.
Used in Chemical Synthesis:
(1R,3aR,7aR)-1-((R)-6-hydroxy-6-Methylheptan-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one is utilized as a key intermediate in the synthesis of various complex organic compounds, taking advantage of its unique structural features and reactivity.

Upstream product

• 66774-84-3 de-A,B-25-hydroxycholestan-8β-ol 
• 33813-99-9 Grundmann's alcohol 
• 66251-18-1 Grundmann's ketone 
• 132713-39-4 (1R,3aR,4R,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-ol 
• 70550-66-2 <1R-<1β(R*),3aα,4β,7aβ>>-Octahydro-4-acetoxy-α,α,ε,7a-tetramethyl-1H-indene-1-pentanol 
• 135359-40-9 de-A,B-24-(methoxycarbonyl)-cholestan-8β-ol 
• 307953-25-9 8β-[(tert-butyldimethylsilyl)oxy]-de-A,B-cholestan-25-ol 
• 81506-39-0 (R)-4-((1R,3aR,4R,7aR)-4-Hydroxy-7a-methyl-octahydro-inden-1-yl)-pentanal 
• 83685-49-8 (1R,3aR,4R,7aR)-1-((R)-1,5-Dimethyl-hex-4-enyl)-7a-methyl-octahydro-inden-4-ol 
• 81506-36-7 Acetic acid (3aR,4R,7aS)-1-eth-(Z)-ylidene-7a-methyl-octahydro-inden-4-yl ester 
• 81506-33-4 Acetic acid (3aR,4R,7aS)-7a-methyl-1-oxo-octahydro-inden-4-yl ester 
• 70550-65-1 Acetic acid (1R,3aR,4S,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-yl ester 
• 146434-14-2 <1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol 
• 146434-07-3 (1R,7aR)-1-((R)-3-Hydroxy-1-methyl-propyl)-7a-methyl-1,2,5,6,7,7a-hexahydro-inden-4-one 

Downstream Products

• 144848-24-8 25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one 
• 157380-23-9 (1R,3aR,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-octahydro-indene 
• 157380-24-0 25-Hydroxy-14-epi-vitamin D₃ 
• 157380-25-1 1alpha,25-Dihydroxy-14-epi-vitamin D₃ 
• 104121-92-8 Eldecalcitol 

Relevant academic research and scientific papers

Synthesis of vitamin D3 analogues with A-ring modifications to directly measure vitamin D levels in biological samples

C-3-substituted 25-hydroxyvitamin D3 analogues were synthesized as tools to directly measure levels of vitamin D in biological samples. The strategy involves vinyloxycarbonylation of the 3β-hydroxy group and formation of a carbamate bond with a hydroxyl or amino group at the end of the alkyl chain. Biotinylated conjugates of synthesized derivatives were generated to be linked with vitamin D binding protein (DBP). The spacer group present in the alkyl chain is important in the binding of antibodies to the analogue-DBP complex. When compared to 25-hydroxyvitamin D3-DBP, the binding of some antibodies to the analogue-DBP complex of the 25-hydroxyvitamin D 3 derivative 10 that posses an 8-aminoctyl alkyl chain is significantly reduced, but this analogue displaced [26,27-3H]-25- hydroxyvitamin D3 from DBP. In contrast, the 8-hydroxyoctyl alkyl chain analogue 9 showed less displacement.

Large-Scale Synthesis of Eldecalcitol

Industrial-scale synthesis of eldecalcitol is described. AA highly diastereoselective epoxidation of p-methoxybenzyl (PMB) protected dienol at room temperature provides the key epoxide intermediate with a secondary hydroxyl group, which is alkylated with a triflate to set up all of the subunits at the C-1, C-2, and C-3 positions of the A-ring fragment. Selective protecting group manipulation followed by palladium-catalyzed cyclization then provides the A-ring synthon. The C/D-ring fragment is obtained by (1) direct C-H hydroxylation of Grundman's ketone using in situ prepared trifluoropropanone dioxirane and (2) protection. Finally, the coupling of the A-ring with the C/D-ring fragment, global deprotection, and recrystallization provide the highly crystalline eldecalcitol.

Total synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71)

A convergent method for the synthesis of ED-71 has been developed. Starting from the reported epoxide 5 which could be easily prepared from D-mannitol, ED-71 was synthesized in 11 linear steps with 17% overall yield.

Synthesis and evaluation of third generation vitamin D3 analogues as inhibitors of Hedgehog signaling

The Hedgehog (Hh) pathway is a developmental pathway with therapeutic potential as a target for a variety of cancers. In recent years, several vitamin D-based compounds have been identified as potent inhibitors of Hh signaling. These analogues contain aromatic phenol A-ring mimics coupled to the CD-ring side chain of vitamin D3 through modified seco-B regions. To continue structure-activity relationship studies on this class of Hh pathway inhibitors, multiple series of vitamin D-based analogues that contain an amine-based seco-B tether and/or incorporate a hydroxyl moiety on C-25 were designed and synthesized. These compounds were evaluated in multiple cell lines for their anti-Hh activity, and we identify analogues 16, 21, 22 as potent vitamin D-based Hh inhibitors (IC50 values of 110–340 nM). We also performed a series of mechanism of action studies in knockout cell lines to further explore whether these analogues inhibit the Hh pathway through a known Hh pathway component or the vitamin D receptor. While the specific cellular target that mediates these effects remains elusive, our studies suggest multiple cellular targets may mediate the anti-Hh activity of this scaffold.

Compounds, conjugates, reagent kit and application of reagent kit

The invention discloses compounds, conjugates, a reagent kit for detecting vitamin D and an application of the reagent kit in detecting the vitamin D. The compounds have a structure represented by a formula (1) in the description, wherein L represents a linking arm, R1, R2 and R3 are independently selected from hydrogen, hydroxyl, C1-C3 alkoxy, C1-C3 alkyl, C2-C3 alkenyl and C2-C3 alkynyl. The compounds provided by the invention can accurately detect the vitamin D.

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.

Fluoride-mediated elimination of allyl sulfones: Application to the synthesis of a 2,4-dimethyl-A-ring vitamin D3 analogue

A coupling strategy for the synthesis of 2,4-dimethyl-1α,25(OH) 2D3 is achieved which involves methylation of a pro-A ring vinyl sulfone and in situ traping of the allyl sulfonyl anion with a CD ring allyl chloride. TBAF-promoted 1,2-eliminative desulfonylation and concomitant silyl ether deprotection gives the vitamin D3 analogue.

Synthesis of C-11 linked active ester derivatives of vitamin D3 and their conjugations to 42-residue helix-loop-helix peptides

Derivatives of vitamin D3 carrying an 8-carbon linker at C-11 terminating in an active ester were synthesized from commercial vitamin D3 using a disassembly-reassembly strategy. Vitamin D3 was cleaved at the C6-C7 double b

Pd-catalyzed carbocyclization-negishi cross-coupling cascade: A novel approach to 1α,25-dihydroxyvitamin D3 and analogues

(Chemical Equation Presented) A mild palladium-catalyzed cascade has been used for the synthesis of the hormone 1α,25-dihydroxyvitamin D3 (calcitriol, 1a) and its analogues 1b and 1c. This one-pot process involves two consecutive transformations at room temperature: An initial palladium-catalyzed 6-exo-cyclocarbopalladation of vinyl triflates followed by a Negishi cross-coupling reaction with an alkenyl zinc. This novel strategy opens new possibilities for the preparation of a variety of new vitamin D analogues of therapeutic potential, particularly with modifications at the triene and/or ring-A.