(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

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Chemical Name:(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate
CAS No.:245672-19-9
Molecular Formula:C₂₅H₄₅NO₅SSi
Molecular Weight:499.788
Hs Code.:

Synonyms:(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

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Chemical Property of (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

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Technology Process of (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

There total 13 articles about (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate 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: 90.0%

: 245672-18-8
(+/-)-[1-[8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octynyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

: 245672-19-9
(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: With sodium tetrahydroborate; hydrogen; nickel diacetate; In ethanol; for 7h;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

: 3282-30-2
pivaloyl chloride

: 245672-19-9
(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 87 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 54 h / 20 °C

2.1: FeCl₃ / 0.25 h

3.1: 12.5 g / aq. NaOH / methanol / 0.5 h / 15 °C

4.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂

5.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

5.2: 7.49 g / tetrahydrofuran / 1 h

6.1: 73 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 15 °C

7.1: FeCl₃

8.1: dimethylsulfide; TFA / CH₂Cl₂ / 9 h / 20 °C

9.1: 4.91 g / aq. NaOH / methanol / 0.5 h / 20 °C

10.1: 90 percent / Ni(OAc)2; NaBH₄; H₂ / aq. ethanol / 7 h

With dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethylsulfide; hydrogen; nickel diacetate; iron(III) chloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: Esterification / 2.1: Elimination / 3.1: Deacetylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Addition / 6.1: Substitution / 7.1: Elimination / 8.1: Substitution / 9.1: Deacetylation / 10.1: Reduction;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

: 245672-15-5
[1-(formylmethyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

: 245672-19-9
(+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: 7.49 g / tetrahydrofuran / 1 h

2.1: 73 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 15 °C

3.1: FeCl₃

4.1: dimethylsulfide; TFA / CH₂Cl₂ / 9 h / 20 °C

5.1: 4.91 g / aq. NaOH / methanol / 0.5 h / 20 °C

6.1: 90 percent / Ni(OAc)2; NaBH₄; H₂ / aq. ethanol / 7 h

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; hydrogen; nickel diacetate; iron(III) chloride; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: Metallation / 1.2: Addition / 2.1: Substitution / 3.1: Elimination / 4.1: Substitution / 5.1: Deacetylation / 6.1: Reduction;
DOI:10.1016/S0040-4020(99)00455-X