215509-33-4

Usage

Uses

Used in Organic Synthesis:
(2S)-2-((1R,3aR,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique structure and functional groups make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S)-2-((1R,3aR,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol is utilized as a key component in the development of new drugs. Its specific stereochemistry and functional groups can be exploited to design molecules with novel biological activities and selectivity, potentially leading to the discovery of new therapeutic agents.
Used in Material Science:
(2S)-2-((1R,3aR,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol is also used in material science for the development of new materials with specialized properties. (2S)-2-((1R,3aR,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol's unique structure and functional groups can be incorporated into the design of advanced materials for applications in areas such as nanotechnology, polymer science, and electronic devices.
Used in Chemical Research:
In the realm of chemical research, (2S)-2-((1R,3aR,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol serves as a subject of study for understanding the fundamental aspects of organic chemistry, stereochemistry, and reaction mechanisms. Its unique structure provides an opportunity to explore new synthetic methodologies and investigate the properties of complex organic molecules.

Upstream product

• 100928-02-7 (24R,22E)-de-A,B-8β-<(tert-butyldimethylsilyl)oxy>ergost-22-ene 
• 104651-47-0 (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100928-03-8 (S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol 
• 66774-80-9 (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate 
• 108-48-5 2,6-dimethylpyridine 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 185997-26-6 (1R,3aR,7aR)-1-((S)-1-hydroxypropan-2-yl)-7a-methyloctahydro-1H-inden-4-ol 
• 1315461-12-1 methyl (2S)-2-[(1S,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl]propanoate 
• 1315461-10-9 methyl [(1S,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl]acetate 
• 1315461-08-5 [(1S,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl]acetic acid 
• 1315461-06-3 methyl (1S,1aS,1bR,5S,5aR,6aR)-5-(tert-butyldimethylsilyloxy)-1b-methyldecahydrocyclopropa[a]indene-1-carboxylate 
• 1315461-04-1 methyl (1S,1aS,1bR,5S,5aR,6aR)-5-hydroxy-1b-methyldodecahydrocycloprop[a]indene-1-carboxylate 

Downstream Products

• 171011-48-6 (1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(R)-2-hydroxy-1-methylethyl]-7a-methyl-1H-indene 
• 214351-86-7 (1R,4S,7aR)-4-(tert-butyldimethylsilyloxy)octahydro-1-((R)-1-iodopropan-2-yl)-7a-methyl-1H-indene 
• 182510-45-8 20-epi-25-hydroxyvitamin D₃ 
• 182510-44-7 20-epi-vitamin D₃ 
• 1454816-54-6 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-chlorobenzoate 

Relevant academic research and scientific papers

Design and efficient synthesis of novel vitamin D analogues bearing an aniline moiety in their side chains

Six novel vitamin D analogues bearing an aniline moiety in their side chains were designed and synthesized using a convergent route. The CD ring fragments were prepared from Inhoffen-Lythgoe diol in five- or six-steps with high yields. Secondary amines we

Modified Julia olefination and α aminoxylation reactions mediated convergent synthesis of 1α, 24 (R)-dihydroxyvitamin D3 (tacalcitol)

A convergent synthesis of tacalcitol has been achieved starting from inexpensive and commercially available isovaleraldehyde and easily available Inhoffen-Lythgoe diol. Key steps include a proline catalyzed α aminoxylation and a Julia-Kocienski olefination.

A new metabolite of Paricalcitol: stereoselective synthesis of (22Z)-isomer of 1α,25-dihydroxy-19-norvitamin D2

Stereoselective synthesis of (22Z)-isomer of Paricalcitol, an analog of 1,25-dihydroxyergocalciferol, an active form of vitamin D2 (Ergocalciferol) has been described. The two key critical synthetic steps involved are Julia–Lythgoe's Wittig–Hor

Mild and selective deprotection of tert -butyl(dimethyl)silyl ethers with catalytic amounts of sodium tetrachloroaurate(III) dihydrate

A simple and mild method for the removal of tert-butyl(dimethyl)silyl (TBS) protecting groups with catalytic amounts of sodium tetrachloroaurate(III) dihydrate is described. The procedure permits selective deprotection of aliphatic TBS ethers in good to excellent yields in the presence of aromatic TBS ethers, aliphatic triisopropylsilyl ethers, aliphatic tert-butyl(diphenyl)silyl ethers, or sterically hindered aliphatic TBS ethers. Additionally, TBS ethers can also be transformed into 4-methoxybenzyl ethers or methyl ethers in one pot by using larger quantities of the catalyst and a higher reaction temperature.

Synthesis of Denosomin-Vitamin D3 Hybrids and Evaluation of Their Anti-Alzheimer's Disease Activities

As an extension of previously conducted studies on developing an anti-Alzheimer's disease agent, denosomin (1-deoxy-24-norsominone, an artificial inducer of neurite elongation), derivatives were designed and synthesized based on the hypothesis that our denosomin would exhibit axonal extension activity via a 1,25D3-membrane-associated, rapid response steroid-binding protein (1,25D3-MARRS) pathway. The biological assay revealed that the hybridization of characteristic δ-lactone in denosomin and the triene moiety in VD3 was effective to enhance the nerve re-extension activity in amyloid β (Aβ)-damaged neurons.

Analogues of the Inhoffen-Lythgoe diol with anti-proliferative activity

The anti-proliferative activity of a series of ester- and amide-linked Inhoffen-Lythgoe side chain analogues is reported. Whereas the Inhoffen-Lythgoe diol was inactive in these studies, a number of aromatic and aliphatic ester-linked side chains demonstr

Synthesis of a trans-hydrindanone, precursor for the preparation of vitamin D analogues

We developed a very efficient and practical method for the large-scale synthesis of a trans-hydrindan derivative related to vitamin D, based on the Criegee rearrangement. This ketone is a valuable synthon for the preparation of Gemini-type vitamin D analogues or other calcitriol analogues modified at C-20, C-21 or the D-ring. Our methodology is superior to those previously reported when considering efficiency and expediency. The Criegee rearrangement was the key step for a large-scale synthesis of a trans-hydrindan derivative related to vitamin D. This work is superior to previous approaches with regards to efficiency and expediency. Copyright

Design, synthesis, evaluation, and structure of vitamin D analogues with furan side chains

Based on the crystal structures of human vitamin D receptor (hVDR) bound to 1α,25-dihydroxy-vitamin D3 (1,25 D) and superagonist ligands, we previously designed new superagonist ligands with a tetrahydrofuran ring at the side chain that optimize the aliphatic side-chain conformation through an entropy benefit. Following a similar strategy, four novel vitamin D analogues with aromatic furan side chains (3 a, 3 b, 4 a, 4 b) have now been developed. The triene system has been constructed by an efficient stereoselective intramolecular cyclization of an enol triflate (A-ring precursor) followed by a Suzuki-Miyaura coupling of the resulting intermediate with an alkenyl boronic ester (CD-side chain, upper fragment). The furan side chains have been constructed by gold chemistry. These analogues exhibit significant pro-differentiation effects and transactivation potency. The crystal structure of 3 a in a complex with the ligand-binding domain of hVDR revealed that the side-chain furanic ring adopts two conformations. Copyright

Total synthesis of a CD-ring: Side-chain building block for preparing 17-epi-calcitriol derivatives from the Hajos-Parrish dione

An efficient synthesis of the key building block for 17-epi-calctriol from the Hajos-Parrish dione involving a sequence of diastereoselective transformation of the azulene core and the side-chain construction is presented.

Synthesis and preliminary biological evaluation of 20-epi-eldecalcitol [20-epi-1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3: 20-epi-ED-71]

Eldecalcitol [1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3, developing code: ED-71] is an analog of active vitamin D3, 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3] that possesses a hydroxypropoxy substituent at the 2β-position of 1,25(OH)2D3. Eldecalcitol has potent biological effects on bone and is now in preparation for approval as a promising medicine for the treatment of osteoporosis in Japan. To explore chemical structure-biological activity relationships between eldecalcitol and related analogs, we have already synthesized 1-epi-eldecalcitol, 3-epi-eldecalcitol, and 1,3-diepi-eldecalcitol with inherent biological interests of each targeted analog and evaluated their biological responses. It has been reported that 20-epi-1,25(OH)2D3, a diastereomer of 1,25(OH)2D3 that possesses an inverted methyl substituent at the 20-position of the side chain, shows remarkably enhanced biological activities compared to parental compound, 1,25(OH)2D3. As a continuation of our modification studies on eldecalcitol, we took great interest in 20-epi-eldecalcitol and its biological responses. In this paper, the synthesis of 20-epi-eldecalcitol by the Trost coupling reaction between the A-ring fragment and the C/D-ring fragment as well as in vitro preliminary biological evaluation of 20-epi-eldecalcitol are described. In the induction of human myeloid leukemia cell (HL-60) differentiation, inhibition of the human histiocytic lymphoma cell (U937) proliferation, and increase in osteocalcin concentration in the human osteosarcoma cell (MG-63), 20-epi-eldecalcitol showed significantly enhanced activity compared to eldecalcitol.