(E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester
• CAS No.: 420118-99-6
• Molecular Formula: C₂₄H₂₇Cl₂NO₅
• Molecular Weight: 480.388
• Mol file: 420118-99-6.mol

Synonyms:(E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

Chemical Property of (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

There total 2 articles about (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl 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: 80.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + Boc-Tyr(Cl2-Bzl)-H (143961-89-1) → (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester (420118-99-6)

Guidance literature:

In dimethyl sulfoxide; at 25 ℃; for 2h;

DOI:10.1246/cl.2002.130

Reference yield:

[2-[4-(2,6-dichloro-benzyloxy)-phenyl]-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester → (E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester (420118-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / 25 °C

2: 80 percent / dimethylsulfoxide / 2 h / 25 °C

With lithium aluminium tetrahydride; In diethyl ether; dimethyl sulfoxide; 2: Wittig;

DOI:10.1246/cl.2002.130

Reference yield:

(E)-(S)-4-tert-Butoxycarbonylamino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester (420118-99-6) → (E)-(S)-4-Amino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester (420119-00-2)

Guidance literature:

With hydrogenchloride; at 25 ℃; for 1h;

DOI:10.1246/cl.2002.130

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

Boc-Tyr(Cl₂-Bzl)-H

Downstream raw materials:

(E)-(S)-4-Amino-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

(E)-(S)-4-((R)-2-Amino-3-phenyl-propionylamino)-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

(E)-(S)-4-((R)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-5-[4-(2,6-dichloro-benzyloxy)-phenyl]-pent-2-enoic acid methyl ester

{(2S,3S,6R)-6-Benzyl-3-[4-(2,6-dichloro-benzyloxy)-benzyl]-5-oxo-piperazin-2-yl}-acetic acid methyl ester