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

Base Information

• Chemical Name: (3R,4R,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide
• CAS No.: 1351186-30-5
• Molecular Formula: C₄₀H₅₄N₂O₂S
• Molecular Weight: 626.947
• Mol file: 1351186-30-5.mol

Synonyms:

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

There total 18 articles about (3R,4R,6S)-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,4R,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-30-5)

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,4R,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-30-5)

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:

C24H37NOSi → (3R,4R,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-30-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diethyl cyanophosphonate; triethylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

6.2: -78 - -40 °C / Inert atmosphere

7.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 12 h / 20 °C

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

With dmap; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water; 4.1: Swern oxidation / 4.2: Swern oxidation / 5.2: Horner-Wadsworth-Emmons olefination;

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

((2R,4S)-6-azido-2,4-dimethylhexyloxy)(tert-butyl)diphenylsilane

Downstream raw materials:

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