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

Base Information

• Chemical Name: (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate, p-toluenesulfonate (ester)
• CAS No.: 245672-20-2
• Molecular Formula: C₃₂H₅₁NO₇S₂Si
• Molecular Weight: 653.977

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

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

Chemical Property:

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

There total 14 articles about (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate, p-toluenesulfonate (ester) 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: 93.0%

p-toluenesulfonyl chloride (98-59-9) + (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-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, p-toluenesulfonate (ester) (245672-20-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4.5h;

DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

pivaloyl chloride (3282-30-2) → (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate, p-toluenesulfonate (ester) (245672-20-2)

Guidance literature:

Multi-step reaction with 11 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

11.1: 93 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 4.5 h / 20 °C

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 / 11.1: Esterification;

DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

[1-(formylmethyl)-2,5-cyclohexadiene-1-yl]methyl pivalate (245672-15-5) → (+/-)-[1-[(Z)-8-hydroxy-2-[2-(trimethylsilyl)ethanesulfonamido]-3-octenyl]-2,5-cyclohexadiene-1-yl]methyl pivalate, p-toluenesulfonate (ester) (245672-20-2)

Guidance literature:

Multi-step reaction with 7 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

7.1: 93 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 4.5 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; hydrogen; nickel diacetate; iron(III) chloride; triethylamine; 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 / 7.1: Esterification;

DOI:10.1016/S0040-4020(99)00455-X

upstream raw materials:

p-toluenesulfonyl chloride

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

pivaloyl chloride

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

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