tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

Base Information

Chemical Name:tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)
CAS No.:245672-17-7
Molecular Formula:C₃₄H₅₉NO₇SSi
Molecular Weight:653.996
Hs Code.:

tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

Synonyms:tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

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Chemical Property of tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

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Technology Process of tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

There total 9 articles about tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (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: 73.0%

: 145387-82-2
N-(tert-butyloxycarbonyl)(2-trimethylsilylethyl)sulfonamide

: 245672-16-6
(+/-)-[1-(8-tert-butoxy-2-hydroxy-3-octynyl)-2,5-cyclohexadiene-1-yl]methyl pivalate

: 245672-17-7
tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 15 ℃; for 4h;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

: 3282-30-2
pivaloyl chloride

: 245672-17-7
tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

Guidance literature:: Multi-step reaction with 6 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

With dmap; sodium hydroxide; n-butyllithium; oxalyl dichloride; iron(III) chloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Esterification / 2.1: Elimination / 3.1: Deacetylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Addition / 6.1: Substitution;
DOI:10.1016/S0040-4020(99)00455-X

Reference yield:

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

: 245672-17-7
tert-butyl-(+/-)-[7-tert-butoxy-1-[[1-(hydroxymethyl)-2,5-cyclohexadiene-1-yl]methyl]-2-heptynyl][[2-(trimethylsilyl)ethyl]sulfonyl]carbamate, pivalate (ester)

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1.1: Metallation / 1.2: Addition / 2.1: Substitution;
DOI:10.1016/S0040-4020(99)00455-X