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

Base Information

• Chemical Name: (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate
• CAS No.: 1425558-17-3
• Molecular Formula: C₃₄H₄₈N₂O₆
• Molecular Weight: 580.765
• Mol file: 1425558-17-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate 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: 99.0%

(R)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-hydroxyoctanamide (1425558-16-2) + Boc-N-Me-Phe-OH (37553-65-4) → (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate (1425558-17-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo3027643

Reference yield:

(R)-2-(1-(benzyloxy)-4-((4-methoxybenzyl)oxy)butan-2-yl)-isoindoline-1,3-dione (1425558-12-8) → (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate (1425558-17-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 20 °C

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

2.2: 24 h / 20 - 35 °C

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

4.1: 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

4.2: 3 h / 20 °C / Inert atmosphere

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

6.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; ortho-nitrophenyl selenocyanate; tributylphosphine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; methylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo3027643

Reference yield:

(R)-5-((tert-butyldimethylsilyl)oxy)octanoic acid (1425558-05-9) → (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((tert-butoxycarbonyl)-(methyl)-amino)-3-phenyl propanoate (1425558-17-3)

Guidance literature:

Multi-step reaction with 3 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

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 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-(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

(3S,6S,10R,16R)-3-benzyl-10-(hydroxymethyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclo-hexadecane-2,5,12-trione