(1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol

Base Information

• Chemical Name: (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol
• CAS No.: 134458-49-4
• Molecular Formula: C₂₇H₄₂O₃
• Molecular Weight: 414.629
• Mol file: 134458-49-4.mol

Synonyms:(1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol

Chemical Property of (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol

There total 13 articles about (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(3R,3aR,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene (530147-10-5) → (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol (134458-49-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1039/b209147j

Reference yield: 70.0%

1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether (134458-47-2) → (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol (134458-49-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 21h; Ambient temperature;

DOI:10.1021/ja00018a038

Reference yield:

de-A,B-25-cholesta-8,25-dien-8-yl trifluromethanesulfonate (113490-28-1) → (1R,3S)-5-[(1R,3aR,7aR)-1-((1R)-5-hydroxy-1,5-dimethylhexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethynyl-4-methylcyclohex-4-ene-1,3-diol (134458-49-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) mercuric acetate, 2.) aq. NaOH, NaBH₄ / 1.) THF, H₂O, RT, 1 h, 2.) THF, H₂O, RT, 30 min

2: 84 percent / diethylamine, CuI, bispalladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature

3: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; bispalladium(II) acetate; mercury(II) diacetate; tetrabutyl ammonium fluoride; diethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00018a038

upstream raw materials:

1α-<((tert-butyldiphenyl)silyl)oxy>-6,7-dehydro-25-hydroxyprevitamin D3 (tert-butyldiphenyl)silyl ether

(3R,3aR,7aR)-7-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-cyclohex-1-enylethynyl]-3-((R)-1,5-dimethyl-5-triethylsilanyloxy-hexyl)-3a-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene

(1R,3aR,7aR)-1-[(2R)-6-hydroxy-6-methylhept-2-yl]-7a-methyloctahydroinden-4-one

25-[(triethylsilyl)oxy]de-A,B-cholestan-8-one

Downstream raw materials:

calcitriol