bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

Base Information

• Chemical Name: bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate
• CAS No.: 1377990-61-8
• Molecular Formula: C₃₀H₃₉Cl₂NO₁₄
• Molecular Weight: 708.544
• Mol file: 1377990-61-8.mol

Synonyms:bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

Chemical Property of bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate

There total 10 articles about bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[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: 76.0%

chloromethyl isopropyl carbonate (35180-01-9) + (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid (1377990-58-3) → bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (1377990-61-8)

Guidance literature:

With potassium carbonate; sodium iodide; In N,N-dimethyl-formamide; for 18h; Product distribution / selectivity;

Reference yield:

(1S,2S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-oxobicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-04-6) → bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (1377990-61-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: L-Selectride / tetrahydrofuran / 2 h / 0 °C / Industry scale; Inert atmosphere

1.2: 2.67 h / 0 °C

2.1: triethylamine / tetrahydrofuran / 0 - 20 °C

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

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

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

6.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

7.1: potassium carbonate; methanol / 16 h / 20 °C

8.1: hydrogenchloride; water / 1,4-dioxane / 4.5 h / 100 °C

9.1: triethylamine / 1,4-dioxane; water / 20 - 50 °C

10.1: potassium carbonate / sodium iodide / N,N-dimethyl-formamide / 18 h

With 4-methyl-morpholine; hydrogenchloride; methanol; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; L-Selectride; potassium carbonate; triethylamine; triphenylphosphine; silver(l) oxide; osmium(VIII) oxide; tetrabutylammomium bromide; sodium iodide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 6.1: Mitsunobu reaction;

Reference yield:

(1S,2S,4S,5R,6R)-di-tert-butyl 2-[(tert-butoxycarbonyl)amino]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (635318-05-7) → bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate (1377990-61-8)

Guidance literature:

Multi-step reaction with 9 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: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C

6: potassium carbonate; methanol / 16 h / 20 °C

7: water; acetic acid / Reflux

8: sodium hydrogencarbonate / 1,4-dioxane; water / 432 h / 20 °C

9: potassium carbonate / sodium iodide / N,N-dimethyl-formamide / 18 h

With 4-methyl-morpholine; methanol; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine; silver(l) oxide; osmium(VIII) oxide; tetrabutylammomium bromide; sodium iodide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 5: Mitsunobu reaction;

upstream raw materials:

chloromethyl isopropyl carbonate

(1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid

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

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

Downstream raw materials:

bis({[(1-methylethoxy)carbonyl]oxy}methyl) (1S,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)oxy]-4-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylate hydrochloride