(2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol

Base Information

• Chemical Name: (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol
• CAS No.: 1297531-55-5
• Molecular Formula: C₄₃H₇₈O₄Si₂
• Molecular Weight: 715.261
• Mol file: 1297531-55-5.mol

Synonyms:(2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol

Chemical Property of (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol

There total 26 articles about (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-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:

(1S,2S,3E,6S,8S,9Z)-1-(3,5-bis((triisopropylsilyl)oxy)phenyl)-10-cyclohexyl-2,6,8-trimethyldeca-3,9-diene-1,5-diol (1297531-48-6) → (1S,2S,6S,8S,Z)-1-(3,5-bis((triisopropylsilyl)oxy)phenyl)-10-cyclohexyl-1-hydroxy-2,6,8-trimethyldec-9-en-5-one (1297531-49-7) + (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol (1297531-55-5)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; methyllithium; In tetrahydrofuran; diethyl ether; at 20 - 60 ℃; for 4.7h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200834p

Reference yield:

tert-butyl(((2S,4S)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentyl)oxy)diphenylsilane (1297531-62-4) → (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol (1297531-55-5)

Guidance literature:

Multi-step reaction with 10 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

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; tris(triphenylphosphine)ruthenium(II) chloride; C₅H₅N*HO₃S; 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) → (2R,5S,6S)-6-(3,5-bis((triisopropylsilyl)oxy)phenyl)-2-((2S,4S,Z)-6-cyclohexyl-4-methylhex-5-en-2-yl)-5-methyltetrahydro-2H-pyran-2-ol (1297531-55-5)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; tris(triphenylphosphine)ruthenium(II) chloride; C₅H₅N*HO₃S; 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

Downstream raw materials:

((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)

((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)

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