pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

Base Information

• Chemical Name: pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester
• CAS No.: 1585181-30-1
• Molecular Formula: C₆₂H₆₉Cl₃N₂O₁₀S
• Molecular Weight: 1140.66
• Mol file: 1585181-30-1.mol

Synonyms:pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

Chemical Property of pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

There total 27 articles about pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester 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: 80.0%

pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-5-hydroxy-3-methylhex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585180-89-7) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-30-1)

Guidance literature:

With dmap; In pyridine; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm4019965

Reference yield:

1-((9H-fluoren-9-yl)methyl)2-((3S,5S)-9-(((S)-5-(allyloxy)-5-oxo-1-(tritylthio)pentan-2-yl)amino)-7-hydroxy-2,2,5-trimethyl-9-oxononan-3-yl)(2S)-pyrrolidine-1,2-dicarboxylate + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-30-1) + 1-((9H-fluoren-9-yl)methyl)2-((3S,5S)-9-(((S)-5-(allyloxy)-5-oxo-1-(tritylthio)pentan-2-yl)amino)-2,2,5-trimethyl-9-oxo-7-(((2,2,2-trichloroethoxy)carbonyl)oxy)nonan-3-yl) (2S)-pyrrolidine-1,2-dicarboxylate

Guidance literature:

1-((9H-fluoren-9-yl)methyl)2-((3S,5S)-9-(((S)-5-(allyloxy)-5-oxo-1-(tritylthio)pentan-2-yl)amino)-7-hydroxy-2,2,5-trimethyl-9-oxononan-3-yl)(2S)-pyrrolidine-1,2-dicarboxylate; With pyridine; In dichloromethane; at 0 ℃; for 0.166667h;

2,2,2-Trichloroethyl chloroformate; With dmap; at 0 ℃; for 1h; Overall yield = 90 %;

DOI:10.1021/acs.orglett.6b02780

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-5,5-dimethyl-hexan-2-ol → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-30-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: triethylamine / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

2.1: potassium tert-butylate / toluene / 1 h / Inert atmosphere; Reflux

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere; Molecular sieve

4.1: triethylamine / diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

5.1: titanium(IV) isopropylate / dichloromethane / 1 h / Inert atmosphere; Reflux

5.2: 4 h / Inert atmosphere; Reflux

6.1: copper(l) cyanide / diethyl ether / 2.33 h / -78 °C / Inert atmosphere; Cooling with ice

6.2: 3.33 h / -78 - -20 °C / Inert atmosphere

7.1: trimethylaluminum / dichloromethane; hexane / -78 - 20 °C / Inert atmosphere

7.2: 6.67 h / 0 - 20 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 °C / Inert atmosphere

9.2: 0.5 h / -78 °C / Inert atmosphere

10.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 2 h / 0 °C / Inert atmosphere

10.2: 0.5 h / 20 °C

11.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

12.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Inert atmosphere

13.1: N-ethyl-N,N-diisopropylamine; 2,4,6-trichlorobenzoyl chloride / toluene / 0.5 h / 20 °C / Inert atmosphere

13.2: 3 h / 10 - 20 °C / Inert atmosphere

14.1: Oxone; sodium hydrogencarbonate; osmium(VIII) oxide / N,N-dimethyl-formamide; tert-butyl alcohol / 15 h / 20 °C / Inert atmosphere

14.2: 5 h / 20 °C

15.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

16.1: pyridine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; Oxone; osmium(VIII) oxide; trifluorormethanesulfonic acid; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

upstream raw materials:

pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S)-6-[(1S)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-5-hydroxy-3-methylhex-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester

2,2,2-Trichloroethyl chloroformate

(S)-tert-butyl (1-tert-butylbut-3-enyloxy)dimethylsilane

(3S)-2,2-dimethyl-5-hexen-3-ol

Downstream raw materials:

apratoxin S₇