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

Base Information

Chemical Name: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
CAS No.:1377990-35-6
Molecular Formula:C₂₉H₄₁Cl₂NO₁₀S
Molecular Weight:666.617
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 92.0%

: 1377990-31-2
di-tert-butyl (1S,2R,3S,4R,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

: 124-63-0
methanesulfonyl chloride

: 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

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/j.bmcl.2016.10.067

Reference yield:

: 1377990-28-7
(1S,2S,5R,6S)-di-t-butyl 2-((t-butoxycarbonyl)amino)bicyclo-[3.1.0]hex-3-ene-2,6-dicarboxylate

: 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

Guidance literature:: Multi-step reaction with 3 steps

1: water; 4-methyl-morpholine / osmium(VIII) oxide / tert-butyl alcohol; acetone / 5 h / 20 °C

2: silver(l) oxide / tetrabutylammomium bromide / N,N-dimethyl-formamide / 20 °C

3: triethylamine / tetrahydrofuran / 0 - 20 °C

With 4-methyl-morpholine; water; triethylamine; silver(l) oxide; osmium(VIII) oxide; tetrabutylammomium bromide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

Reference yield:

: 635318-05-7
(1S,2S,4S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

: 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

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine / tetrahydrofuran / 0 - 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / Reflux

3: water; 4-methyl-morpholine / osmium(VIII) oxide / tert-butyl alcohol; acetone / 5 h / 20 °C

4: silver(l) oxide / tetrabutylammomium bromide / N,N-dimethyl-formamide / 20 °C

5: triethylamine / tetrahydrofuran / 0 - 20 °C

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; water; triethylamine; silver(l) oxide; osmium(VIII) oxide; tetrabutylammomium bromide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;