5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol

Base Information

• Chemical Name: 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol
• CAS No.: 1297531-41-9
• Molecular Formula: C₂₅H₃₈O₄
• Molecular Weight: 402.574
• Mol file: 1297531-41-9.mol

Synonyms:5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol

Chemical Property of 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol

There total 28 articles about 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-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: 98.0%

((5-((2S,3S,6S,8S,9S,11S)-8-((S)-cyclohexyliodomethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl)-1,3-phenylene)bis(oxy))bis(triisopropylsilane) (1297531-56-6) → 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol (1297531-41-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h;

DOI:10.1021/ol200834p

Reference yield:

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane (1297531-62-4) → 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol (1297531-41-9)

Guidance literature:

Multi-step reaction with 13 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

2: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

3: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

4: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

6: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

7: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

8: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

9: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2.5 h / 20 °C

10: tris(triphenylphosphine)ruthenium(II) chloride; methyllithium / tetrahydrofuran; diethyl ether / 4.7 h / 20 - 60 °C / Inert atmosphere

11: N-iodo-succinimide / dichloromethane / 25 h / 0 - 20 °C / Darkness

12: 2,2'-azobis(isobutyronitrile); triphenylstannane / benzene / 15 h / Inert atmosphere; Reflux

13: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; 2,2'-azobis(isobutyronitrile); C₅H₅N*HO₃S; triphenylstannane; tetrabutyl ammonium fluoride; water; methyllithium; iodine; pyridinium p-toluenesulfonate; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene; 3: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

Reference yield:

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol (765915-18-2) → 5-((2S,3S,6R,8R,9S,11S)-8-(cyclohexylmethyl)-3,9,11-trimethyl-1,7-dioxaspiro[5.5]undecan-2-yl) benzene-1,3-diol (1297531-41-9)

Guidance literature:

Multi-step reaction with 12 steps

1: C₅H₅N*HO₃S; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C

2: chromium dichloride; nickel dichloride / tetrahydrofuran; dimethyl sulfoxide / 17 h / 20 °C / Inert atmosphere; Large scale reaction

3: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

4: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C

5: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; acetonitrile / 20 °C / Darkness

6: lithium carbonate / acetonitrile; benzene / 60 h / Reflux

7: lithium hexamethyldisilazane / tetrahydrofuran; toluene / -78 - 0 °C / Inert atmosphere

8: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2.5 h / 20 °C

9: tris(triphenylphosphine)ruthenium(II) chloride; methyllithium / tetrahydrofuran; diethyl ether / 4.7 h / 20 - 60 °C / Inert atmosphere

10: N-iodo-succinimide / dichloromethane / 25 h / 0 - 20 °C / Darkness

11: 2,2'-azobis(isobutyronitrile); triphenylstannane / benzene / 15 h / Inert atmosphere; Reflux

12: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; tris(triphenylphosphine)ruthenium(II) chloride; 2,2'-azobis(isobutyronitrile); C₅H₅N*HO₃S; triphenylstannane; tetrabutyl ammonium fluoride; water; methyllithium; iodine; pyridinium p-toluenesulfonate; lithium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene; 2: Nozaki-Hiyama-Kishi reaction;

DOI:10.1021/ol200834p

upstream raw materials:

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane

(2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanal

(S)-3-((S,E)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-2-enoyl)-isopropyloxazolidin-2-one