(-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate

Base Information

• Chemical Name: (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate
• CAS No.: 1312025-89-0
• Molecular Formula: C₂₈H₃₆N₂O₄S
• Molecular Weight: 496.671
• Mol file: 1312025-89-0.mol

Synonyms:(-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate

Chemical Property of (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate

There total 2 articles about (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate 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: 92.0%

(+)-(S)-O-3-phenyl-1-(tri-n-butylstannyl)propyl pyrrolidine-1-carbothioate (169140-88-9,1071508-50-3,1071508-47-8) + (-)-(S)-S-4-nitrophenyl 2-(tert-butoxycarbonyl)amino-3-phenylpropanethioate (1279668-23-3) → (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate (1312025-89-0)

Guidance literature:

With copper(I) thiophene-2-carboxylate; In 1,4-dioxane; at 100 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol201330j

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate (1312025-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24.25 h / 0 - 20 °C

2: copper(I) thiophene-2-carboxylate / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere

With copper(I) thiophene-2-carboxylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ol201330j

Reference yield: 72.0%

(-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate (1312025-89-0) → (-)-tert-butyl (2S,3R,4R)-3,4-dihydroxy-1,6-diphenylhexan-2-ylcarbamate (128414-07-3)

Guidance literature:

(-)-O-(3R,5S)-5-(tert-butoxycarbonyl)amino-4-oxo-1,6-diphenylhexan-3-yl pyrrolidine-1-carbothioate; With L-Selectride; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;

With dihydrogen peroxide; In tetrahydrofuran; water; at 50 ℃; for 4h;

With sodium hydroxide; In tetrahydrofuran; water; for 12h;

DOI:10.1021/ol201330j

upstream raw materials:

(+)-(S)-O-3-phenyl-1-(tri-n-butylstannyl)propyl pyrrolidine-1-carbothioate

(-)-(S)-S-4-nitrophenyl 2-(tert-butoxycarbonyl)amino-3-phenylpropanethioate

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(-)-tert-butyl (2S,3R,4R)-3,4-dihydroxy-1,6-diphenylhexan-2-ylcarbamate