(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-iodo-propyl)-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-(3-iodo-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
• CAS No.: 213915-68-5
• Molecular Formula: C₂₇H₄₃IO₃
• Molecular Weight: 542.541
• Mol file: 213915-68-5.mol

Synonyms:

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

There total 13 articles about (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-iodo-propyl)-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: 20.0%

(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (164228-46-0) → (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-iodo-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-68-5) + (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-iodomethyl-6-(3-iodo-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In benzene; at 50 ℃; for 0.416667h;

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-(3-iodo-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-68-5)

Guidance literature:

Multi-step reaction with 12 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.) Al(CH₃)3, 2,6-diphenylphenol / 1.) CH₂Cl₂, hexane, 0 deg C, 1 h, 2.) CH₂Cl₂, hexane, 0 deg C, 1.5 h

4: 86 percent / tetra-n-butylammonium fluoride hydrate / tetrahydrofuran / 0.33 h / 0 °C

5: 1.) Hg(OAc)2, 2.) NaBH₄, NaOMe / 1.) THF, RT, 24 h, 2.) THF, MeOH, -78 deg C, 15 min

6: 80 percent / aq. tetra-n-butylammonium hydroxide / CH₂Cl₂ / 3 h / Ambient temperature

7: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

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

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

10: NaBH₄ / ethanol / 1 h / Ambient temperature

11: NaBH₄, tetrakis(triphenylphsophine)palladium⁽⁰⁾ / tetrahydrofuran / 6 h / Ambient temperature

12: 80 percent / I₂, Ph₃P, imidazole / benzene / 0.42 h / 50 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl iodide; (1,1';3',1''-terphenyl)-2'-ol; mercury(II) diacetate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; iodine; trimethylaluminum; sodium methylate; sodium tert-pentoxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; tert-butyl alcohol; trichloroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm960677q

Reference yield:

(1R,9R,12R)-5-(1,1-Dimethyl-heptyl)-12-(3-hydroxy-1-methylene-propyl)-8-oxa-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-3,9-diol (213915-85-6) → (6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-iodo-propyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol (213915-68-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Hg(OAc)2, 2.) NaBH₄, NaOMe / 1.) THF, RT, 24 h, 2.) THF, MeOH, -78 deg C, 15 min

2: 80 percent / aq. tetra-n-butylammonium hydroxide / CH₂Cl₂ / 3 h / Ambient temperature

3: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / Ambient temperature

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

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

6: NaBH₄ / ethanol / 1 h / Ambient temperature

7: NaBH₄, tetrakis(triphenylphsophine)palladium⁽⁰⁾ / tetrahydrofuran / 6 h / Ambient temperature

8: 80 percent / I₂, Ph₃P, imidazole / benzene / 0.42 h / 50 °C

With 1H-imidazole; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; mercury(II) diacetate; tetra(n-butyl)ammonium hydroxide; iodine; sodium methylate; sodium tert-pentoxide; Dess-Martin periodane; triphenylphosphine; trichloroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1021/jm960677q

upstream raw materials:

(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-propyl)-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

(1R,9R,12R)-5-(1,1-Dimethyl-heptyl)-12-(3-hydroxy-1-methylene-propyl)-8-oxa-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-3,9-diol

(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-6-(2-hydroxy-ethyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromene-1,9-diol