(R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide

Base Information

• Chemical Name: (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide
• CAS No.: 1425558-16-2
• Molecular Formula: C₁₉H₂₉NO₃
• Molecular Weight: 319.444
• Mol file: 1425558-16-2.mol

Synonyms:(R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide

Chemical Property of (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide

There total 9 articles about (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide 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: 82.0%

(R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-((tert-butyldimethylsilyl)oxy)octanamide (1425558-15-1) → (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide (1425558-16-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/jo3027643

Reference yield:

(S)-1-(benzyloxy)-4-((4-methoxybenzyl)oxy)butan-2-ol (251571-58-1) → (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide (1425558-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C

3.1: ortho-nitrophenyl selenocyanate; tributylphosphine / tetrahydrofuran / 1.25 h / 20 - 35 °C / Inert atmosphere

3.2: 24 h / 20 - 35 °C

4.1: methylamine / ethanol / 2 h / 20 °C / Inert atmosphere

5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere

5.2: 3 h / 20 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With ortho-nitrophenyl selenocyanate; tributylphosphine; di-isopropyl azodicarboxylate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; methylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Mitsunobu Displacement;

DOI:10.1021/jo3027643

Reference yield:

(R)-5-((tert-butyldimethylsilyl)oxy)octanoic acid (1425558-05-9) → (R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide (1425558-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.08 h / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 3.5 h / 0 °C / Inert atmosphere

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo3027643

upstream raw materials:

(S)-1-(benzyloxy)-4-((4-methoxybenzyl)oxy)butan-2-ol

(R)-2-(1-(benzyloxy)-4-((4-methoxybenzyl)oxy)butan-2-yl)-isoindoline-1,3-dione

(R)-5-((tert-butyldimethylsilyl)oxy)octanoic acid

(R)-2-(1-(benzyloxy)but-3-en-2-yl)isoindoline-1,3-dione

Downstream raw materials:

(S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate

(S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-(methylamino)-3-phenyl propanoate

(S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((S)-N,2-dimethylpent-4-enamido)-3-phenyl propanoate

(3S,6S,10R,16R)-3-benzyl-10-((benzyloxy)-methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione