tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane
CAS No.:753016-54-5
Molecular Formula:C₃₅H₅₀O₃Si
Molecular Weight:546.866
Hs Code.:

Synonyms:tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

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Chemical Property of tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

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Technology Process of tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

There total 12 articles about tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane 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: 91.0%

: 217640-00-1
(2R,3S)-6-Isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

: 213740-17-1
(3Z,5R)-(+)-3-bromomethyl-7-tert-butyldiphenylsilyloxy-5-methylhept-3-ene

: tert-Butyl-[(4Z,6Z)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

: 753016-54-5
tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

Guidance literature:: (3Z,5R)-(+)-3-bromomethyl-7-tert-butyldiphenylsilyloxy-5-methylhept-3-ene; With tributylphosphine; In acetonitrile; at 20 ℃; for 0.75h;

(2R,3S)-6-Isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde; With potassium tert-butylate; In tetrahydrofuran; toluene; at 0 ℃; for 0.75h;
DOI:10.1021/ol049219z

Reference yield:

: 71565-21-4
(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

: 753016-54-5
tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 10 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: PPh₃; Zn powder / CH₂Cl₂ / 24 h / 20 °C

2.2: 440.7 mg / CH₂Cl₂ / 2 h / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 93 percent / tetrahydrofuran / -78 - 20 °C

4.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

5.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

5.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

5.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

6.1: 82 percent / DIBAL / CH₂Cl₂ / -78 °C

7.1: 85 percent / PPTS / benzene

8.1: 85 percent / TBAF / tetrahydrofuran

9.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

9.2: 98 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: Bu₃P / acetonitrile / 0.75 h / 20 °C

10.2: 91 percent / tBuOK / toluene; tetrahydrofuran / 0.75 h / 0 °C

With n-butyllithium; oxalyl dichloride; tributylphosphine; Dowex 50W X₈; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene; 10.2: Wittig olefination;
DOI:10.1021/ol049219z

Reference yield:

: 753016-50-1
(R)-4-((S)-3,3-Dibromo-1-methyl-allyl)-2,2-dimethyl-[1,3]dioxolane

: 753016-54-5
tert-Butyl-[(4Z,6E)-(R)-5-ethyl-7-((2S,3S)-6-isopropoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methyl-hepta-4,6-dienyloxy]-diphenyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

1.2: 93 percent / tetrahydrofuran / -78 - 20 °C

2.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

3.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

3.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

3.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

4.1: 82 percent / DIBAL / CH₂Cl₂ / -78 °C

5.1: 85 percent / PPTS / benzene

6.1: 85 percent / TBAF / tetrahydrofuran

7.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

7.2: 98 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: Bu₃P / acetonitrile / 0.75 h / 20 °C

8.2: 91 percent / tBuOK / toluene; tetrahydrofuran / 0.75 h / 0 °C

With n-butyllithium; oxalyl dichloride; tributylphosphine; Dowex 50W X₈; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; benzene; 8.2: Wittig olefination;
DOI:10.1021/ol049219z