(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

Base Information

• Chemical Name: (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
• CAS No.: 213915-67-4
• Molecular Formula: C₂₆H₄₁IO₃
• Molecular Weight: 528.514
• Mol file: 213915-67-4.mol

Synonyms:

Chemical Property of (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

There total 12 articles about (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol 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: 73.0%

(6S,6aR,9R,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(1,1-dimethyl-heptyl)-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-83-4) → (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-67-4)

Guidance literature:

With hydrogen fluoride; triethylamine hydrofluoride; In acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1021/jm960677q

Reference yield:

(1R,4R,5R)-4-(2,6-dihydroxy-4-(2-methyloctan-2-yl)phenyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-one (182509-23-5) → (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-67-4)

Guidance literature:

Multi-step reaction with 11 steps

1: 83 percent / imidazole, DMAP / dimethylformamide / 36 h / Ambient temperature

2: 1.) TMSI, t-BuOH, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CCl₄, 0 deg C, 1.5 h, 2.) C₆H₆, 50 deg C, 3 h

3: 1.) sodium tert-amylate / 1.) C₆H₆, RT, 15 min, 2.) C₆H₆, 70 deg C, 3 h

4: aq. CCl₃CO₂H / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 72 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

6: 100 percent / imidazole / dimethylformamide / 17 h / Ambient temperature

7: 1.) Al(CH₃)3, 2,6-diphenylphenol / 1.) CH₂Cl₂, hexane, 0 deg C, 1 h, 2.) CH₂Cl₂, hexane, 0 deg C, 2 h

8: 95 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 2 h / -78 °C

9: 1.) Hg(OAc)2, 2.) 40percent aq. tetra-n-butylammonium hydroxide, aq. NaOH, NaBH₄ / 1.) THF, RT, 24 h, 2.) CH₂Cl₂, 0 deg C, 5 min

10: 82 percent / I₂, Ph₃P, imidazole / benzene / 0.75 h / 45 °C

11: 73 percent / Et₃N*HF, 49percent aq. HF / acetonitrile / 1.5 h / 0 °C

With 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl iodide; (1,1';3',1''-terphenyl)-2'-ol; hydrogen fluoride; mercury(II) diacetate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; iodine; trimethylaluminum; sodium tert-pentoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine hydrofluoride; triphenylphosphine; tert-butyl alcohol; trichloroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1021/jm960677q

Reference yield:

2-[(1R,2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(3-hydroxy-1-methylene-propyl)-cyclohexyl]-5-(1,1-dimethyl-heptyl)-benzene-1,3-diol (213915-81-2) → (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-67-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Hg(OAc)2, 2.) 40percent aq. tetra-n-butylammonium hydroxide, aq. NaOH, NaBH₄ / 1.) THF, RT, 24 h, 2.) CH₂Cl₂, 0 deg C, 5 min

2: 82 percent / I₂, Ph₃P, imidazole / benzene / 0.75 h / 45 °C

3: 73 percent / Et₃N*HF, 49percent aq. HF / acetonitrile / 1.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; hydrogen fluoride; mercury(II) diacetate; tetra(n-butyl)ammonium hydroxide; iodine; triethylamine hydrofluoride; triphenylphosphine; In acetonitrile; benzene;

DOI:10.1021/jm960677q

upstream raw materials:

(6S,6aR,9R,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(1,1-dimethyl-heptyl)-6-(2-iodo-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

(1R,4R,5R)-4-(2,6-dihydroxy-4-(2-methyloctan-2-yl)phenyl)-6,6-dimethylbicyclo[3.1.1]heptan-2-one

2-[(1R,2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(3-hydroxy-1-methylene-propyl)-cyclohexyl]-5-(1,1-dimethyl-heptyl)-benzene-1,3-diol

(6S,6aR,9R,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(1,1-dimethyl-heptyl)-6-(2-hydroxy-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol