ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate

Base Information

• Chemical Name: ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate
• CAS No.: 1585181-21-0
• Molecular Formula: C₃₁H₃₅NO₄S
• Molecular Weight: 517.689

Synonyms:ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate

Chemical Property of ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate

There total 4 articles about ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate 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: 88.0%

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal (149910-63-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate (1585181-21-0)

Guidance literature:

In toluene; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm4019965

Reference yield:

N-tert-butyloxycarbonyl-S-trityl-L-cysteine (21947-98-8,87494-13-1) → ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate (1585181-21-0)

Guidance literature:

Multi-step reaction with 3 steps

1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3: toluene / 3 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jm4019965

Reference yield:

(R)-N-methyl-N-methoxy-2-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionamide (158861-38-2) → ethyl (R,E-)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-penta-2-enoate (1585181-21-0)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2: toluene / 3 h / 0 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; In tetrahydrofuran; toluene;

DOI:10.1021/jm4019965

upstream raw materials:

N-α-(tert-butoxycarbonyl)-S-(triphenylmethyl)-L-cysteinal

ethyl (triphenylphosphoranylidene)acetate

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

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

Downstream raw materials:

apratoxin S₁₀

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

C₂₉H₃₃NO₄S

ethyl (R)-4-tert-butoxycarbonylamino-5-(triphenylmethylthio)-pentanonate

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