tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

Base Information

Chemical Name:tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate
CAS No.:134078-66-3
Molecular Formula:C₂₅H₃₇NO₆S
Molecular Weight:479.638
Hs Code.:

Synonyms:tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

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Chemical Property of tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

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Technology Process of tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

There total 7 articles about tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate 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: 92.0%

: 18303-04-3
N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

: 134078-65-2
(2Z,4E)-8-(pivaloyloxy)-2,4-octadienol

: 134078-66-3
tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1021/jo00014a051

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 134078-66-3
tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1: 1) BuLi / 1) THF, -78 deg C, 15 min, 2) r.t., 2 h

2: 1) DIBAH, 2) I₂, 3) NaOMe

3: 94 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

4: 83 percent / Et₃N, (PPh₃)2PdCl₂, CuI / 4 h / Ambient temperature

5: 1) Sia₂BH, 2) AcOH, 3) 30percent H₂O₂, 6N NaOH

6: 92 percent / PPh₃, DEAD / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; n-butyllithium; dihydrogen peroxide; iodine; sodium methylate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00014a051

Reference yield:

: 13224-84-5
5-trimethylsilanyl-pent-4-yn-1-ol

: 134078-66-3
tert-butyl N-<(2Z,4E)-8-(pivaloyloxy)-2,4-octadienyl>-N-(p-toluenesulfonyl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: 1) DIBAH, 2) I₂, 3) NaOMe

2: 94 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 83 percent / Et₃N, (PPh₃)2PdCl₂, CuI / 4 h / Ambient temperature

4: 1) Sia₂BH, 2) AcOH, 3) 30percent H₂O₂, 6N NaOH

5: 92 percent / PPh₃, DEAD / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; dihydrogen peroxide; iodine; sodium methylate; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; acetic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00014a051