(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

Base Information

Chemical Name:(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester
CAS No.:745794-23-4
Molecular Formula:C₁₉H₂₆N₂O₆
Molecular Weight:378.425
Hs Code.:

Synonyms:(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

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Chemical Property of (1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

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Technology Process of (1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

There total 11 articles about (1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]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: 86.0%

: 745794-22-3
(1R,2R,3S,5S)-{3-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-6-oxabicyclo[3.1.0]hex-2-yl}carbamic acid tert-butyl ester

: 745794-23-4
(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/jo0496547

Reference yield:

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

: 745794-23-4
(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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

9: 78 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 24 h / 15 °C

10: 86 percent / D-camphor-10-sulfonic acid / CH₂Cl₂ / 24 h / 20 °C

With copper diacetate; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 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

: 745794-23-4
(1R,5S,6R,7R)-[7-hydroxy-4-(4-methoxybenzyl)-3-oxo-2-oxa-4-azabicyclo[3.2.1]oct-6-yl]carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

10: 78 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 24 h / 15 °C

11: 86 percent / D-camphor-10-sulfonic acid / CH₂Cl₂ / 24 h / 20 °C

With copper diacetate; oxalyl dichloride; camphor-10-sulfonic acid; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 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