(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

Base Information

Chemical Name:(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal
CAS No.:1315317-36-2
Molecular Formula:C₃₂H₄₄O₂Si
Molecular Weight:488.786
Hs Code.:

Synonyms:(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

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Chemical Property of (3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

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Technology Process of (3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

There total 19 articles about (3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal 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%

: 1315317-51-1
(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dien-1-ol

: 1315317-36-2
(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol201547q

Reference yield:

: 1033074-47-3
(S)-1-((5,5-dibromo-3-methylpent-4-enyloxy)methyl)-4-methoxybenzene

: 1315317-36-2
(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

2.3: 0 °C / Inert atmosphere; Saturated solution

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / aq. phosphate buffer

5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

6.1: copper(l) cyanide / diethyl ether / 1 h / -78 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

7.2: 24 h / 0 - 20 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; copper(l) cyanide; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 7.1: Wittig reaction;
DOI:10.1021/ol201547q

Reference yield:

: 1033074-22-4
(S)-1-methoxy-4-((3-methylpent-4-ynyloxy)methyl)benzene

: 1315317-36-2
(3S,4E,8S,10E)-12-(tert-butyldiphenylsilyloxy)-3,4,8-trimethyl-6-methylenedodeca-4,10-dienal

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

1.3: 0 °C / Inert atmosphere; Saturated solution

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / aq. phosphate buffer

4.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

5.1: copper(l) cyanide / diethyl ether / 1 h / -78 °C / Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

6.2: 24 h / 0 - 20 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 0 °C / Inert atmosphere

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; tetrapropylammonium perruthennate; copper(l) cyanide; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; 6.1: Wittig reaction;
DOI:10.1021/ol201547q