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

Base Information

• Chemical Name: (3S,6R,10R,16S)-3-benzyl-10-((benzyloxy)methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione
• CAS No.: 1425558-22-0
• Molecular Formula: C₃₃H₄₄N₂O₅
• Molecular Weight: 548.723
• Mol file: 1425558-22-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (3S,6R,10R,16S)-3-benzyl-10-((benzyloxy)methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione 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:

(S)-(S)-8-(((R)-1-(benzyloxy)but-3-en-2-yl)amino)-8-oxooctan-4-yl-2-(methylamino)-3-phenyl propanoate (1425558-09-3) → (3S,6R,10R,16S)-3-benzyl-10-((benzyloxy)methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione (1425558-22-0)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 5 h / 20 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 h / Reflux; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; toluene; 2.1: |Grubbs Olefin Metathesis;

DOI:10.1021/jo3027643

Reference yield:

(R)-2-methylpent-4-enoic acid (63527-49-1) → (3S,6R,10R,16S)-3-benzyl-10-((benzyloxy)methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione (1425558-22-0)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 5 h / 20 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 h / Reflux; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; toluene; 2.1: |Grubbs Olefin Metathesis;

DOI:10.1021/jo3027643

Reference yield:

(R)-2-(1-(benzyloxy)-4-((4-methoxybenzyl)oxy)butan-2-yl)-isoindoline-1,3-dione (1425558-12-8) → (3S,6R,10R,16S)-3-benzyl-10-((benzyloxy)methyl)-4,6-dimethyl-16-propyl-1-oxa-4,11-diazacyclohexadec-8-ene-2,5,12-trione (1425558-22-0)

Guidance literature:

Multi-step reaction with 9 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: 3.5 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

6.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

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

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

8.2: 5 h / 20 °C / Inert atmosphere

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 20 h / Reflux; Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; ortho-nitrophenyl selenocyanate; chlorotriisopropylsilane; tributylphosphine; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; HATU; methylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 9.1: |Grubbs Olefin Metathesis;

DOI:10.1021/jo3027643

upstream raw materials:

(S)-(S)-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

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

(S)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-5-((tert-butyldimethylsilyl)oxy)octanamide

Downstream raw materials:

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