benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

Base Information

Chemical Name:benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate
CAS No.:1423738-93-5
Molecular Formula:C₃₀H₄₇NO₅
Molecular Weight:501.707
Hs Code.:

Synonyms:benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

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Chemical Property of benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

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Technology Process of benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

There total 4 articles about benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate 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: 65.0%

: 1423738-88-8
benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate

: 97780-30-8
(12-hydroxydodecyl)triphenylphosphonium bromide

: 1423738-93-5
benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

Guidance literature:: (12-hydroxydodecyl)triphenylphosphonium bromide; With lithium hexamethyldisilazane; In tetrahydrofuran; at -60 ℃; for 0.666667h; Inert atmosphere;

benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate; In tetrahydrofuran; at -60 ℃; for 2h; Inert atmosphere;
DOI:10.1007/s00726-012-1349-0

Reference yield:

: 30925-18-9
2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester

: 1423738-93-5
benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide; pyridine / acetonitrile; tetrahydrofuran / 1 h / -30 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: toluene / 3.5 h / 70 °C / Inert atmosphere

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -60 °C / Inert atmosphere

3.2: 2 h / -60 °C / Inert atmosphere

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; acetonitrile; 2.1: |Wittig Olefination / 3.2: |Wittig Olefination;
DOI:10.1007/s00726-012-1349-0

Reference yield:

: 3344-77-2
12-bromododecanol

: 1423738-93-5
benzyl (2S)-2-(tert-butoxycarbonylamino)-18-hydroxy-octadeca-4,6-dienoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: ethanol / 48 h / Reflux; Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -60 °C / Inert atmosphere

2.2: 2 h / -60 °C / Inert atmosphere

With lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; 2.2: |Wittig Olefination;
DOI:10.1007/s00726-012-1349-0