(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

Base Information

Chemical Name:(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate
CAS No.:745794-20-1
Molecular Formula:C₃₁H₄₀N₂O₇
Molecular Weight:552.668
Hs Code.:

Synonyms:(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

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Chemical Property of (4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

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Technology Process of (4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

There total 9 articles about (4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate 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: 93.0%

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 745794-13-2
{(1R,2S)-2-[Benzyloxycarbonyl-(4-methoxy-benzyl)-amino]-1-formyl-pent-4-enyl}-carbamic acid tert-butyl ester

: 745794-20-1
(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

Guidance literature:: In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo0496547

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 745794-20-1
(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

Guidance literature:: Multi-step reaction with 7 steps

1: 8.1 g / MgSO₄ / CH₂Cl₂ / 20 °C

2: 87 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -70 °C

3: Zn; Cu(OAc)2; AcOH / H₂O / 2 h / 70 °C

4: NaHCO₃ / H₂O; ethyl acetate / 20 °C

5: 8.64 g / p-TsOH*H₂O / methanol / 1 h / Heating

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂

7: 93 percent / tetrahydrofuran / 20 °C

With copper diacetate; oxalyl dichloride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 6: Swern oxidation;
DOI:10.1021/jo0496547

Reference yield:

: 108149-63-9
4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 745794-20-1
(4S,5S,2E)-ethyl 5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-4-(tert-butoxycarbonylamino)octa-2,7-dienate

Guidance literature:: Multi-step reaction with 8 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 8.1 g / MgSO₄ / CH₂Cl₂ / 20 °C

3: 87 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -70 °C

4: Zn; Cu(OAc)2; AcOH / H₂O / 2 h / 70 °C

5: NaHCO₃ / H₂O; ethyl acetate / 20 °C

6: 8.64 g / p-TsOH*H₂O / methanol / 1 h / Heating

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂

8: 93 percent / tetrahydrofuran / 20 °C

With copper diacetate; oxalyl dichloride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1: Swern oxidation / 7: Swern oxidation;
DOI:10.1021/jo0496547