(2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid

Base Information

• Chemical Name: (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid
• CAS No.: 263023-28-5
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 263023-28-5.mol

Synonyms:(2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid

Chemical Property of (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid

There total 9 articles about (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid 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%

(1-formyl-pent-4-enyl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester → (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid (263023-28-5)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; tert-butyl alcohol; at 25 ℃; for 15h;

DOI:10.1016/S0957-4166(99)00525-X

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid (263023-28-5)

Guidance literature:

Multi-step reaction with 8 steps

1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.33 h / -60 °C

2: 80 percent / 2 h / Heating

3: 82 percent / DIBALH / hexane / 1.5 h / 20 °C

4: tert-butyl hydroperoxide; 4 A molecular sieves; D-(-)-diisopropyl tartrate, titanium tetraisopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -20 °C

5: titanium tetraisopropoxide / CH₂Cl₂ / 48 h / Heating

6: 80 percent / NaHCO₃ / methanol / 4 h / Irradiation

7: aq. NaIO₄ / tetrahydrofuran / 2 h / 20 °C

8: 87 percent / sodium chlorite; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; tert-butyl alcohol; 1: Oxidation / 2: Condensation / 3: Reduction / 4: Epoxidation / 5: Addition / 6: Acylation / 7: Oxidation / 8: Oxidation;

DOI:10.1016/S0957-4166(99)00525-X

Reference yield:

4-pentenal (2100-17-6) → (2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid (263023-28-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / 2 h / Heating

2: 82 percent / DIBALH / hexane / 1.5 h / 20 °C

3: tert-butyl hydroperoxide; 4 A molecular sieves; D-(-)-diisopropyl tartrate, titanium tetraisopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -20 °C

4: titanium tetraisopropoxide / CH₂Cl₂ / 48 h / Heating

5: 80 percent / NaHCO₃ / methanol / 4 h / Irradiation

6: aq. NaIO₄ / tetrahydrofuran / 2 h / 20 °C

7: 87 percent / sodium chlorite; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; tert-butyl alcohol; 1: Condensation / 2: Reduction / 3: Epoxidation / 4: Addition / 5: Acylation / 6: Oxidation / 7: Oxidation;

DOI:10.1016/S0957-4166(99)00525-X

upstream raw materials:

n-Pent-4-enyl alcohol

4-pentenal

di-tert-butyl dicarbonate

(E)-hepta-2,6-dienoic acid methyl ester

Downstream raw materials:

(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester

(2S)-2-[tert-butoxycarbonyl-(4-methoxybenzyl)amino]-5-hexenoic acid methyl ester