di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Base Information

Chemical Name:di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate
CAS No.:1377990-46-9
Molecular Formula:C₃₀H₄₂Cl₂N₂O₉
Molecular Weight:645.577
Hs Code.:

di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

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Chemical Property of di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

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Technology Process of di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

There total 10 articles about di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate 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: 88.0%

: 1377990-46-9
di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Guidance literature:

Reference yield:

: 1377990-35-6
di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methylsulfonyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377990-46-9
di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 144 h / 85 °C

2: trimethylphosphane / tetrahydrofuran; water / 20 °C

3: triethylamine / dichloromethane

With sodium azide; 15-crown-5; triethylamine; trimethylphosphane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2016.10.067

Reference yield:

: 635318-04-6
(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate

: 1377990-46-9
di-tert-butyl (1S,2R,3R,4S,5R,6S)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-[(methoxycarbonyl)amino]bicyclo[3.1.0]hexane-2,6-dicarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: L-Selectride / tetrahydrofuran / 0 °C

2: triethylamine

3: tetrabutyl ammonium fluoride / tetrahydrofuran / Reflux

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water

5: silver(l) oxide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide

6: triethylamine / tetrahydrofuran / 0 - 20 °C

7: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 144 h / 85 °C

8: trimethylphosphane / tetrahydrofuran; water / 20 °C

9: triethylamine / dichloromethane

With osmium(VIII) oxide; sodium azide; 15-crown-5; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; L-Selectride; 4-methylmorpholine N-oxide; triethylamine; silver(l) oxide; trimethylphosphane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2016.10.067