(S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

Base Information

Chemical Name:(S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene
CAS No.:141806-42-0
Molecular Formula:C₂₉H₃₀N₄O₂S
Molecular Weight:498.649
Hs Code.:

(S)-(E)-7-<N-benzyl-N-(benzyloxycarbonyl)amino>-8-azido-3-(phenylthio)octa-1,3-diene

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Chemical Property of (S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

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Technology Process of (S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

There total 8 articles about (S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene 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:

: 77539-18-5,73914-82-6
(S)-(+)-2-benzylamino glutaric acid

: 141806-42-0
(S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / NaHCO₃ / H₂O / 3 h / Ambient temperature

2: 70 percent / BH₃*THF / tetrahydrofuran / 18 h / Ambient temperature

3: 88 percent / pyridine, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

4: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 48 h / Ambient temperature

5: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

6: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

7: 1) 9-BBN, 3) 20percent NaOH / 1) THF, 35-40 deg C, 2 h, 2) r.t., 12 h, 3) 3 h

With pyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; borane-THF; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo00040a045

Reference yield:

: 132316-97-3
(S)-2--1,5-pentanediol

: 141806-42-0
(S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / pyridine, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 48 h / Ambient temperature

3: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

4: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

5: 1) 9-BBN, 3) 20percent NaOH / 1) THF, 35-40 deg C, 2 h, 2) r.t., 12 h, 3) 3 h

With pyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00040a045

Reference yield:

: 132316-96-2
(S)-N-benzyl-N-(benzyloxycarbonyl)glutamic acid

: 141806-42-0
(S)-(E)-7--8-azido-3-(phenylthio)octa-1,3-diene

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / BH₃*THF / tetrahydrofuran / 18 h / Ambient temperature

2: 88 percent / pyridine, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

3: 83 percent / triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 48 h / Ambient temperature

4: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

5: 1) DMSO, oxalyl chloride, 3) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) CH₂Cl₂, -78 deg C, 1 h, 3) CH₂Cl₂, -> r.t., 2 h

6: 1) 9-BBN, 3) 20percent NaOH / 1) THF, 35-40 deg C, 2 h, 2) r.t., 12 h, 3) 3 h

With pyridine; dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; borane-THF; oxalyl dichloride; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00040a045