183506-75-4

Basic information

• Product Name: (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate
• Synonyms: (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate
• CAS NO: 183506-75-4
• Molecular Weight: 480.784
• Mol File: 183506-75-4.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate(183506-75-4)
• EPA Substance Registry System: (R)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahyrdo-1H-inden-1-yl)propyl 4-methylbenzenesulfonate(183506-75-4)

Safety Data

• Hazardous Substances Data: 183506-75-4(Hazardous Substances Data)

Upstream product

• 50-14-6 Calciferol 
• 100928-04-9 (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate 
• 100928-03-8 (S)-2-((1R,3aR,4S,7aR)-4-(tert-butyldimethylsilyloxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol 
• 64190-52-9 (8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol 
• 104651-47-0 (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 
• 98-59-9 p-toluenesulfonyl chloride 
• 171011-48-6 (1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-1-[(R)-2-hydroxy-1-methylethyl]-7a-methyl-1H-indene 
• 189102-76-9 de-A,B-8β,22-di-[(tert-butyldimethyl)silyloxy]-23,24-dinorcholane 

Downstream Products

• 261905-61-7 [(1R,3aR,4S,7aR)-1-((S)-3-Benzenesulfonyl-5-methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-4-yloxy]-tert-butyl-dimethyl-silane 
• 171230-80-1 (1R,3aR,7aR)-7a-Methyl-1-{(R)-1-methyl-2-[3-(1-methyl-1-trimethylsilanyloxy-ethyl)-phenylsulfanyl]-ethyl}-octahydro-inden-4-one 
• 1025981-64-9 (1R,3aR,7aR)-1-{(R)-2-[3-(1-Hydroxy-1-methyl-ethyl)-phenylsulfanyl]-1-methyl-ethyl}-7a-methyl-octahydro-inden-4-one 
• 171011-50-0 (1R,3aR,4S,7aR)-1-{(R)-2-[3-(1-Hydroxy-1-methyl-ethyl)-phenylsulfanyl]-1-methyl-ethyl}-7a-methyl-octahydro-inden-4-ol 

Relevant articles and documents

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

A convergent synthesis of biologically interesting 20-epi-eldecalcitol which possesses an inverted C-21 methyl substituent at the 20-position of the side chain of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (eldecalcitol) is described.

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.

2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol and its uses

This invention provides a novel vitamin D analog, namely, 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol. The compound has the formula: This 2-substituted compound is characterized by relatively high intestinal calcium transport activity and rela

2-Methylene-19-nor-20(S)-25-methyl-1alpha-hydroxycalciferol and its uses

This invention provides a novel vitamin D analog, namely, 2-methylene-19-nor-20(S)-25-methyl-1α-hydroxycalciferol. The compound has the formula: This 2-substituted compound is characterized by relatively high intestinal calcium transport activity and rela

Design and synthesis of novel 20-epi analogues of calcitriol with restricted side chain conformation

The design and efficient preparation of two 20-epi analogues of calcitriol with restricted side chain conformation is described. The formation of the tetrahydropyran ring was achieved via zinc chloride mediated etherification of alcohols. Docking experime

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.

Synthesis and biological activity of 2-methyl-20-epi analogues of 1α,25-dihydroxyvitamin D3

Synthesis and biological evaluation of all eight possible A-ring diastereomers of 2-methyl-20-epi-1,25-dihydroxyvitamin D3 are described. Among the analogues synthesized, 2α-methyl-20-epi-1α,25-dihydroxyvitamin D3 exhibited exceptionally high potency. The double modification of 2- methyl substitution and 20-epimerization yielded analogues with unique activity profiles.

α,25-Dihydroxyvitamin D3 analogs featuring aromatic and heteroaromatic rings: Design, synthesis, and preliminary biological testing

Aromatic compounds 2a-c, analogs of 1α,25-dihydroxyvitamin (calcitriol, 1), and heteroaromatic compounds 4a-c and 5a-c, analogs of 19-nor-1α,25- dihydroxyvitamin D3 (3), were designed to simulate the topology of their biologically potent parent