(4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester

Base Information

• Chemical Name: (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester
• CAS No.: 1333536-82-5
• Molecular Formula: C₃₂H₃₇NO₄S
• Molecular Weight: 531.716
• Mol file: 1333536-82-5.mol

Synonyms:(4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester

Chemical Property of (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester

There total 16 articles about (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl 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: 87.0%

C30H35NO4S + allyl bromide (106-95-6) → (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester (1333536-82-5)

Guidance literature:

C₃₀H₃₅NO₄S; With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 6h;

allyl bromide; With caesium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 10 ℃; for 10h;

Reference yield:

C29H33NO4S (1094435-87-6) + allyl bromide (106-95-6) → (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester (1333536-82-5)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jm4019965

Reference yield:

ethyl (S,E)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate (1333536-81-4) → (4S)-4-N-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanoic acid allyl ester (1333536-82-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / ethanol / 30 h / 20 °C / Inert atmosphere

2: sodium hydroxide; water / ethanol / 2 h / 20 °C / Inert atmosphere

3: potassium carbonate / dimethyl sulfoxide / 5 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; water; potassium carbonate; sodium hydroxide; In ethanol; dimethyl sulfoxide;

DOI:10.1021/jm4019965

upstream raw materials:

C₂₉H₃₃NO₄S

allyl bromide

(S)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide

(R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide

Downstream raw materials:

apratoxin S₄

apratoxin S₁₀

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

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