tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate

Base Information

• Chemical Name: tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate
• CAS No.: 280762-61-0
• Molecular Formula: C₃₆H₄₇N₃O₁₁
• Molecular Weight: 697.783
• Mol file: 280762-61-0.mol

Synonyms:tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate

Chemical Property of tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate

There total 12 articles about tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate 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: 56.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-Amino-3-{3-benzyloxy-5-[(E)-2-((S)-2-oxo-oxazolidin-4-yl)-vinyl]-pyridin-4-yl}-propionic acid methyl ester → tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate (280762-61-0)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃; for 6h;

DOI:10.1016/S0957-4166(99)00329-8

Reference yield:

[5-(benzyloxy)-4-(chloromethyl)-3-pyridinyl]methanol (252987-08-9) → tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate (280762-61-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / n-BuLi / tetrahydrofuran / 5 h / -78 °C

2.1: 62 percent / MnO₂ / CHCl₃ / 20 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / -78 °C

3.2: 72 percent / tetrahydrofuran / 4 h / -78 °C

4.1: 0.5 N aq. HCl / acetonitrile / 0.75 h / 20 °C

5.1: 56 percent / DMAP; Et₃N / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; manganese(IV) oxide; n-butyllithium; triethylamine; In tetrahydrofuran; chloroform; acetonitrile; 1.1: Substitution / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Hydrolysis / 5.1: Acylation;

DOI:10.1016/S0957-4166(99)00329-8

Reference yield:

4-(hydroxymethyl)-5-{[(4-methoxybenzyl)oxy]methyl}-3-pyridinol (252987-06-7) → tert-butyl-(4S)-4-[(E:Z)-2-(5-(benzyloxy)-4-{(2S)-2-[bis(tert-butoxycarbonyl)amio]-3-methoxy-3-oxopropyl}-3-pyridinyl)ethenyl]-2-oxo-1,3-oxazolidine-3-carboxylate (280762-61-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaOEt / ethanol / -78 °C

1.2: xylene / 4 h / Heating

2.1: SOCl₂ / benzene / 0.5 h / Heating

3.1: 58 percent / 0.5 N aq. HCl / 15 h / Heating

4.1: 86 percent / n-BuLi / tetrahydrofuran / 5 h / -78 °C

5.1: 62 percent / MnO₂ / CHCl₃ / 20 h / 20 °C

6.1: n-BuLi / tetrahydrofuran / -78 °C

6.2: 72 percent / tetrahydrofuran / 4 h / -78 °C

7.1: 0.5 N aq. HCl / acetonitrile / 0.75 h / 20 °C

8.1: 56 percent / DMAP; Et₃N / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; manganese(IV) oxide; n-butyllithium; thionyl chloride; sodium ethanolate; triethylamine; In tetrahydrofuran; ethanol; chloroform; acetonitrile; benzene; 1.1: Addition / 1.2: Decomposition / 2.1: Chlorination / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Oxidation / 6.1: Metallation / 6.2: Substitution / 7.1: Hydrolysis / 8.1: Acylation;

DOI:10.1016/S0957-4166(99)00329-8

upstream raw materials:

di-tert-butyl dicarbonate

[5-(benzyloxy)-4-(chloromethyl)-3-pyridinyl]methanol

4-(hydroxymethyl)-5-{[(4-methoxybenzyl)oxy]methyl}-3-pyridinol

5-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine

Downstream raw materials:

methyl-(2S)-3-(3-(benzyloxy)-5-{(E:Z,3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-1-butenyl}-4-pyridinyl)-2-[bis(tert-butoxycarbonyl)amino]propanoate