(3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

Base Information

• Chemical Name: (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide
• CAS No.: 1351186-35-0
• Molecular Formula: C₄₀H₅₄N₂O₂S
• Molecular Weight: 626.947
• Mol file: 1351186-35-0.mol

Synonyms:

Chemical Property of (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

There total 6 articles about (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide 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:

(R)-1-(tritylthio)but-3-en-2-amine (1351186-44-1) + C17H33NO3 → (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-35-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jo201951s

Reference yield:

C28H31NO3S → (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-35-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; lithium chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Reflux

3: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo201951s

Reference yield:

(R)-3-(tert-butoxycarbonylamino)-4-(tritylthio)but-1-en-2-yl trifluoromethanesulfonate (1351186-14-5) → (3R,4S,6R)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; lithium chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere; Reflux

2: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo201951s

upstream raw materials:

(R)-3-(tert-butoxycarbonylamino)-4-(tritylthio)but-1-en-2-yl trifluoromethanesulfonate

(R)-tert-butyl (1-(tritylthio)but-3-en-2-yl)carbamate

(R)-1-(tritylthio)but-3-en-2-amine

(R)-N,2-dimethyl-N-((3R,5S,6R)-3,5,6-trimethyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

Downstream raw materials:

(R)-N,2-dimethyl-N-((3R,5S,6R)-3,5,6-trimethyl-7-((R)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide

Refernces