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

Base Information

• Chemical Name: pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1R)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester
• CAS No.: 1585181-34-5
• Molecular Formula: C₆₃H₇₁Cl₃N₂O₁₀S
• Molecular Weight: 1154.69

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

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

There total 18 articles about pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1R)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hept-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:

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S)-1-tert-butyl-6-carboxy-5-(2,2,2-trichloroethoxycarbonyloxy)-3-methylhept-1-yl]ester 1-(9H-fluoren-9-ylmethyl)ester (1177263-67-0) + C27H29NO2S → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1R)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-34-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); In dichloromethane; at 0 ℃; for 2.5h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/jm4019965

Reference yield:

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate (1177263-65-8) → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1R)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

1.3: 3 h / 10 - 20 °C / Inert atmosphere

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

2.2: 5 h / 20 °C

3.1: ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

With Oxone; osmium(VIII) oxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm4019965

Reference yield:

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol (676324-80-4) → pyrrolidine-1,2-dicarboxylic acid (2S)-2-{(1S,3S,5S,6S)-6-[(1R)-3-allyloxycarbonyl-1-[(triphenylmethylthio)methyl]propylcarbamoyl]-1-tert-butyl-3-methyl-5-(2,2,2-trichloroethoxycarbonyloxy)hept-1-yl}ester 1-(9H-fluoren-9-ylmethyl)ester (1585181-34-5)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

2.3: 3 h / 10 - 20 °C / Inert atmosphere

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

3.2: 5 h / 20 °C

4.1: ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 0 °C / Inert atmosphere

With dmap; Oxone; osmium(VIII) oxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm4019965

upstream raw materials:

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol

(3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(3R,4S,6S,8S)-8-tert-butyl-4-(2,2,2-trichloroethoxycarbonyloxy)-3,6-dimethyloct-1-en-8-yl]ester 1-(9H-fluoren-9-ylmethyl)ester

pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S)-1-tert-butyl-6-carboxy-5-(2,2,2-trichloroethoxycarbonyloxy)-3-methylhept-1-yl]ester 1-(9H-fluoren-9-ylmethyl)ester

Downstream raw materials:

apratoxin S₉

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