(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 120205-60-9
• Molecular Formula: C₃₃H₃₉NO₅
• Molecular Weight: 529.676
• Mol file: 120205-60-9.mol

Synonyms:(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl 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:

Boc-L-Pro-H (69610-41-9,117625-90-8) + (2S)-Propionyloxy-1,1,2-triphenylethanol (120205-59-6) → (S)-2-[(1S,2R)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120294-45-3) + (S)-2-[(1R,2R)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120294-46-4) + (S)-2-[(1S,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120294-44-2) + (S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120205-60-9)

Guidance literature:

With magnesium bromide; lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given; 2.) THF, -95 deg C, 2 h;

DOI:10.1021/ja00196a061

Reference yield:

(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120205-60-9) → dolastatin 10 (110417-88-4)

Guidance literature:

Multi-step reaction with 5 steps

1: BF₃*Et₂O

2: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C

3: H₂ / Pd/C

4: 1.) CF₃CO₂H, 2.) diethyl phosphorocyanidate, TEA / 1.) CH₂Cl₂, 2.) DME, 0 deg C, 1 h; room temp., 2 h

With diethyl cyanophosphonate; TEA; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/ja00196a061

Reference yield:

(S)-2-[(1R,2S)-1-Hydroxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120205-60-9) → N-Boc-(2R,3R,4S)-dolaproine (120205-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O

2: 57 percent / potassium tert-butoxide / tetrahydrofuran / -20 °C

3: H₂ / Pd/C

With boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/ja00196a061

upstream raw materials:

Boc-L-Pro-H

(2S)-Propionyloxy-1,1,2-triphenylethanol

Downstream raw materials:

(S)-2-[(1R,2S)-1-Methoxy-2-((S)-1,2,2-triphenyl-ethoxycarbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

N-Boc-(2R,3R,4S)-dolaproine

tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate

dolastatin 10