(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

Base Information

Chemical Name:(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne
CAS No.:770711-51-8
Molecular Formula:C₂₅H₄₀OSi
Molecular Weight:384.677
Hs Code.:

Synonyms:(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

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Chemical Property of (4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

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Technology Process of (4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

There total 11 articles about (4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne 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: 100.0%

: 770711-58-5
(3R,4R,5E,7S)-1,1-dibromo-3,5,7-trimethyl-4-(t-butyldimethylsilyloxy)-9-phenyl-1,5-nonadiene

: 74-88-4
methyl iodide

: 770711-51-8
(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 12h;
DOI:10.1021/ol048905v

Reference yield:

: 770711-55-2
(S)-4-methyl-6-phenyl-2-hexyne

: 770711-51-8
(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

Guidance literature:: Multi-step reaction with 7 steps

1.1: Cp₂Zr(H)Cl / tetrahydrofuran / 2 h / 60 °C

1.2: 87 percent / 3 h / 45 °C

2.1: tBuOK; nBuLi; (+)-Ipc₂BOMe / tetrahydrofuran; hexane; diethyl ether / 15 h / -78 °C

2.2: 80 percent / NaOAc; H₂O₂ / H₂O; tetrahydrofuran; diethyl ether / 15 h / 23 °C

3.1: 95 percent / imidazole; DMAP / dimethylformamide / 12 h / 23 °C

4.1: 4.18 g / AD-mix-α / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C

5.1: 3.75 g / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 23 °C

6.1: Ph₃P; Zn / CH₂Cl₂ / 6 h / 23 °C

7.1: 100 percent / nBuLi / tetrahydrofuran; hexane / 12 h / -78 - 23 °C

With 1H-imidazole; dmap; sodium periodate; AD-mix-α; Schwartz's reagent; n-butyllithium; potassium tert-butylate; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; zinc; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Brown's asymmetric crotylboration;
DOI:10.1021/ol048905v

Reference yield:

: 770711-54-1
(S)-1,1-dibromo-3-methyl-5-phenyl-1-pentene

: 770711-51-8
(4R,5R,6E,8S)-4,6,8-trimethyl-5-(t-butyldimethylsilyloxy)-10-phenyl-6-decen-2-yne

Guidance literature:: Multi-step reaction with 8 steps

1.1: nBuLi / tetrahydrofuran; hexane / 12 h / -78 - 23 °C

2.1: Cp₂Zr(H)Cl / tetrahydrofuran / 2 h / 60 °C

2.2: 87 percent / 3 h / 45 °C

3.1: tBuOK; nBuLi; (+)-Ipc₂BOMe / tetrahydrofuran; hexane; diethyl ether / 15 h / -78 °C

3.2: 80 percent / NaOAc; H₂O₂ / H₂O; tetrahydrofuran; diethyl ether / 15 h / 23 °C

4.1: 95 percent / imidazole; DMAP / dimethylformamide / 12 h / 23 °C

5.1: 4.18 g / AD-mix-α / 2-methyl-propan-2-ol; H2O / 48 h / 23 °C

6.1: 3.75 g / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 23 °C

7.1: Ph₃P; Zn / CH₂Cl₂ / 6 h / 23 °C

8.1: 100 percent / nBuLi / tetrahydrofuran; hexane / 12 h / -78 - 23 °C

With 1H-imidazole; dmap; sodium periodate; AD-mix-α; Schwartz's reagent; n-butyllithium; potassium tert-butylate; triphenylphosphine; (+)-B-methoxydiisocamphenylborane; zinc; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Brown's asymmetric crotylboration;
DOI:10.1021/ol048905v