(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

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Chemical Name:(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester
CAS No.:745794-07-4
Molecular Formula:C₂₆H₃₂N₂O₅
Molecular Weight:452.55
Hs Code.:

Synonyms:(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

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Chemical Property of (1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

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Technology Process of (1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

There total 10 articles about (1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl 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:

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

: 745794-07-4
(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 35 ℃; for 24h;
DOI:10.1021/jo0496547

Reference yield:

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

: 745794-07-4
(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

8: [Ru(PCy₃)2(=CHPh)Cl₂] / CH₂Cl₂ / 24 h / 35 °C

With copper diacetate; oxalyl dichloride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; zinc; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 6: Swern oxidation / 8: ring-closing metathesis;
DOI:10.1021/jo0496547

Reference yield:

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

: 745794-07-4
(1S,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]cyclopent-2-enyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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

9: [Ru(PCy₃)2(=CHPh)Cl₂] / CH₂Cl₂ / 24 h / 35 °C

With copper diacetate; oxalyl dichloride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; zinc dibromide; zinc; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 1: Swern oxidation / 7: Swern oxidation / 9: ring-closing metathesis;
DOI:10.1021/jo0496547