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

Base Information

• Chemical Name: (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-7-((S)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide
• CAS No.: 1352307-99-3
• Molecular Formula: C₂₁H₃₈N₂OS
• Molecular Weight: 366.612
• Mol file: 1352307-99-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-7-((S)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide 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: 74.0%

(3R,4S,6S)-8-((R)-N,2-dimethylbutanamido)-3,4,6-trimethyl-N-((S)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-16-7) → (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-7-((S)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide (1352307-99-3,247184-89-0)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo201951s

Reference yield:

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one (1351186-11-2) → (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-7-((S)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide (1352307-99-3,247184-89-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: -78 - -40 °C / Inert atmosphere

2.1: lithium borohydride / methanol / 0.5 h / 20 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 - 40 °C

5.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

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

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

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

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

9.2: -78 - 20 °C / Inert atmosphere

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

10.2: 0 - 20 °C / Inert atmosphere

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

11.2: -78 - -40 °C / Inert atmosphere

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

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

14.1: titanium tetrachloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With dmap; lithium borohydride; n-butyllithium; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; titanium tetrachloride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 5.1: Staudinger reaction / 9.1: Swern oxidation / 9.2: Swern oxidation / 10.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jo201951s

Reference yield:

(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one (1351186-13-4) → (R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-7-((S)-4-vinyl-4,5-dihydrothiazol-2-yl)heptyl)butanamide (1352307-99-3,247184-89-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: lithium borohydride / methanol / 0.5 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 12 h / 20 - 40 °C

4.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 20 - 40 °C

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

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

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

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

8.2: -78 - 20 °C / Inert atmosphere

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

9.2: 0 - 20 °C / Inert atmosphere

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

10.2: -78 - -40 °C / Inert atmosphere

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

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

13.1: titanium tetrachloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

With dmap; lithium borohydride; n-butyllithium; sodium azide; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; titanium tetrachloride; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 4.1: Staudinger reaction / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jo201951s

upstream raw materials:

(R)-3-((S,E)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-enoyl)-4-phenyloxazolidin-2-one

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

(R)-3-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexanoyl)-4-phenyloxazolidin-2-one

(R)-2-methylbutyric acid