(S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate

Base Information

• Chemical Name: (S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate
• CAS No.: 1425558-23-1
• Molecular Formula: C₃₅H₄₈N₂O₅
• Molecular Weight: 576.777
• Mol file: 1425558-23-1.mol

Synonyms:(S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate

Chemical Property of (S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate

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-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate

There total 13 articles about (S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate 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: 66.0%

(R)-2-methylpent-4-enoic acid (63527-49-1) + (S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-(methylamino)-3-phenyl propanoate (1425558-18-4) → (S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate (1425558-23-1)

Guidance literature:

(R)-2-methylpent-4-enoic acid; With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Inert atmosphere;

(S)-(R)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-(methylamino)-3-phenyl propanoate; In N,N-dimethyl-formamide; at 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1021/jo3027643

Reference yield:

(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) → (S)-(R)-8-(((R)-1-(benzyloxy)But-3-en-2-yl)amino)-8-oxooctan-4-yl-2-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate (1425558-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere

2.2: 4.5 h / 20 °C / Inert atmosphere

With chlorotriisopropylsilane; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In dichloromethane; 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-((R)-N,2-dimethylpent-4-enamido)-3-phenylpropanoate (1425558-23-1)

Guidance literature:

Multi-step reaction with 5 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

4.1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere

5.2: 4.5 h / 20 °C / Inert atmosphere

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

DOI:10.1021/jo3027643

upstream 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

(R)-2-methylpent-4-enoic acid

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

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

Downstream raw materials:

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