<1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol

Base Information

• Chemical Name: <1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol
• CAS No.: 146434-14-2
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.484

Synonyms:<1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol

Chemical Property of <1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol

There total 20 articles about <1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol 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: 95.0%

<1R-(1α,3aβ,4α,7aα)>-4-(benzyloxy)-1-<(1R)-3-<(tert-butyldiphenylsilyl)oxy>-1-methylpropyl>octahydro-7a-methyl-1H-indene (146434-13-1) → <1R-<1α(R*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol (146434-14-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo00058a032

Reference yield:

(2R,3R)-3-<(1R)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone (131336-04-4) → <1R-<1α(R*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol (146434-14-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

2: 76 percent / NaBrO₂ / H₂O; acetic acid / 7 h / Ambient temperature

3: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

4: 60 percent / KOH / methanol; H₂O / 1) room temperature, 14 h, 2) reflux, 4 h

5: 85 percent / NaBH₄, CeCl₃*7H₂O / ethanol / 0.33 h / -78 °C

6: 80 percent / tert-butyl hydroperoxide, VO(acac)2 / benzene; 1,2-dichloro-ethane / 1 h / 0 °C

7: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1) -78 deg C, 1 h, 2) to room temperature

8: 77 percent / KOH / 9 h / Heating

9: 100 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

10: 84 percent / 4-(dimethylamino)pyridine, pyridine / CH₂Cl₂ / 0.67 h / 0 °C

11: 75 percent / dimethylsulfoxide / 2 h / 100 °C

12: 60 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

13: 85 percent / NaBH₄, CeCl₃*7H₂O / ethanol / 1 h / -78 °C

14: 80 percent / H₂ / RhCl(PPh₃)3 / CH₂Cl₂ / 22 h / 760 Torr / Ambient temperature

15: 88 percent / pyridinium dichromate / CH₂Cl₂ / 1 h / Ambient temperature

16: 100 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

17: 100 percent / KH / tetrahydrofuran / 1) 0 deg C, 30 min, 2) room temperature, 2 h

18: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) chloride; oxalyl dichloride; sodium bromite; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; RhCl(PPh₃)3; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00058a032

Reference yield:

(2R,3R)-3-((R)-3-Hydroxy-1-methyl-propyl)-2-methyl-cyclopentanol → <1R-<1α(R*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-γ,7a-dimethyl-1H-indene-1-propanol (146434-14-2)

Guidance literature:

Multi-step reaction with 17 steps

1: 76 percent / NaBrO₂ / H₂O; acetic acid / 7 h / Ambient temperature

2: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

3: 60 percent / KOH / methanol; H₂O / 1) room temperature, 14 h, 2) reflux, 4 h

4: 85 percent / NaBH₄, CeCl₃*7H₂O / ethanol / 0.33 h / -78 °C

5: 80 percent / tert-butyl hydroperoxide, VO(acac)2 / benzene; 1,2-dichloro-ethane / 1 h / 0 °C

6: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1) -78 deg C, 1 h, 2) to room temperature

7: 77 percent / KOH / 9 h / Heating

8: 100 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

9: 84 percent / 4-(dimethylamino)pyridine, pyridine / CH₂Cl₂ / 0.67 h / 0 °C

10: 75 percent / dimethylsulfoxide / 2 h / 100 °C

11: 60 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

12: 85 percent / NaBH₄, CeCl₃*7H₂O / ethanol / 1 h / -78 °C

13: 80 percent / H₂ / RhCl(PPh₃)3 / CH₂Cl₂ / 22 h / 760 Torr / Ambient temperature

14: 88 percent / pyridinium dichromate / CH₂Cl₂ / 1 h / Ambient temperature

15: 100 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

16: 100 percent / KH / tetrahydrofuran / 1) 0 deg C, 30 min, 2) room temperature, 2 h

17: 95 percent / Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) chloride; oxalyl dichloride; sodium bromite; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; dimethyl sulfoxide; triethylamine; RhCl(PPh₃)3; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00058a032

upstream raw materials:

<1R-(1α,3aβ,4α,7aα)>-4-(benzyloxy)-1-<(1R)-3-<(tert-butyldiphenylsilyl)oxy>-1-methylpropyl>octahydro-7a-methyl-1H-indene

(2R,3R)-3-<(1R)-2-(methoxycarbonyl)-1-methylethyl>-2-methylcyclopentanone

(2R,3R)-3-((R)-3-Hydroxy-1-methyl-propyl)-2-methyl-cyclopentanone

(1S,2R,3S,4R,5R)-3,5-Dimethyl-6-oxo-bicyclo[2.2.1]heptane-2-carboxylic acid

Downstream raw materials:

de-A,B-25-hydroxycholestan-8β-ol

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

<1R-<1α(R^*),3aβ,4α,7aα>>-4-(benzyloxy)octahydro-δ,7a-dimethyl-1H-indene-1-pentenoic acid ethyl ester

(R)-3-((1R,3aR,4S,7aR)-4-Benzyloxy-7a-methyl-octahydro-inden-1-yl)-butyraldehyde

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