(S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester
• CAS No.: 148117-34-4
• Molecular Formula: C₃₆H₄₂N₂O₁₂
• Molecular Weight: 694.736
• Mol file: 148117-34-4.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic 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: 72.0%

2,6-dibromo-1,4-benzoquinone (19643-45-9) + (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → (S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester (148117-34-4)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1016/0040-4039(93)85035-U

Reference yield: 100.0%

(S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester (148117-34-4) → (S)-2-tert-Butoxycarbonylamino-3-(4-{3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-2,5-dihydroxy-phenoxy}-phenyl)-propionic acid methyl ester (148117-35-5)

Guidance literature:

With sodium dithionite; In chloroform; water; for 1h; Ambient temperature;

DOI:10.1016/0040-4039(93)85035-U

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-(4-{5-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-3,6-dioxo-cyclohexa-1,4-dienyloxy}-phenyl)-propionic acid methyl ester (148117-34-4) → (S)-3-(4-{5-((R)-1-Azido-2-hydroxy-ethyl)-3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-2-methoxy-phenoxy}-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / Na₂S₂O₄ / CHCl₃; H₂O / 1 h / Ambient temperature

2: 71 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 87 percent / K₂CO₃ / acetone / 2 h / Heating

4: 84 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

5: 88 percent / pyridine / CH₂Cl₂ / 1 h

6: 86 percent / PdCl₂(PPh₃)2 / dimethylformamide / 6 h / 90 °C

7: dihydroquinine-p-chlorobenzoate, K₂CO₃, K₃Fe(CN)6, OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

8: Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

9: 91 percent / Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

10: 70 percent / LiN₃ / dimethylformamide / 2 h / 60 °C

11: Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; osmium(VIII) oxide; sodium dithionite; lithium azide; dihydroquinidine 9-O-(4-chlorobenzoate); tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/0040-4039(93)85035-U

upstream raw materials:

2,6-dibromo-1,4-benzoquinone

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-3-(4-{3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-2,5-dihydroxy-phenoxy}-phenyl)-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-3-(4-{3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-2-methoxy-5-vinyl-phenoxy}-phenyl)-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-3-(4-{3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-5-hydroxy-2-methoxy-phenoxy}-phenyl)-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-3-{4-[3-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenoxy]-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-phenoxy]-phenyl}-propionic acid methyl ester