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

Base Information

Chemical Name: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
CAS No.:280762-62-1
Molecular Formula:C₃₅H₄₉N₃O₁₀
Molecular Weight:671.788
Hs Code.:

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

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Chemical Property of 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

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Technology Process of 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

There total 14 articles about 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 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: 63.0%

: 280762-61-0
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

: 280762-62-1
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

Guidance literature:: With methanol; caesium carbonate; at 20 ℃; for 2.5h;
DOI:10.1016/S0957-4166(99)00329-8

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 280762-62-1
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

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / DMAP; Et₃N / acetonitrile / 6 h / 20 °C

2: 63 percent / Cs₂CO₃; MeOH / 2.5 h / 20 °C

With methanol; dmap; caesium carbonate; triethylamine; In acetonitrile; 1: Acylation / 2: Hydrolysis;
DOI:10.1016/S0957-4166(99)00329-8

Reference yield:

: 252987-08-9
[5-(benzyloxy)-4-(chloromethyl)-3-pyridinyl]methanol

: 280762-62-1
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

Guidance literature:: Multi-step reaction with 6 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

6.1: 63 percent / Cs₂CO₃; MeOH / 2.5 h / 20 °C

With hydrogenchloride; methanol; dmap; manganese(IV) oxide; n-butyllithium; caesium carbonate; triethylamine; In tetrahydrofuran; chloroform; acetonitrile; 1.1: Substitution / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Hydrolysis / 5.1: Acylation / 6.1: Hydrolysis;
DOI:10.1016/S0957-4166(99)00329-8