tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate

Base Information

• Chemical Name: tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate
• CAS No.: 1618083-60-5
• Molecular Formula: C₄₂H₅₁BN₂O₈
• Molecular Weight: 722.687
• Mol file: 1618083-60-5.mol

Synonyms:tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate

Chemical Property of tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate

There total 11 articles about tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate 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:

3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester (1256336-53-4) + 2-(2-benzyloxycarbonylisoindolin-5-yl)acetic acid (1618083-59-2) → tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (1618083-60-5)

Guidance literature:

2-(2-benzyloxycarbonylisoindolin-5-yl)acetic acid; With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl acetamide; for 1.5h;

3-[(2R)-2-[bis(trimethylsilyl)amino]-2-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl]-2-methoxy-benzoic acid 1,1-dimethylethyl ester; In tetrahydrofuran; N,N-dimethyl acetamide; for 4h;

Reference yield:

4-bromo-o-xylene (583-71-1) → tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (1618083-60-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 18 h / Reflux

2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 1.5 h / 20 - 60 °C

2.2: 18 h / 20 - 60 °C

3.1: propionic acid; phenol; hydrogen bromide / water / 10 h / Reflux

4.1: N-ethyl-N,N-diisopropylamine / hexane; dichloromethane / 2 h

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 4 h / 72 °C / Inert atmosphere

6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol / 3 h

7.1: sodium periodate / tetrahydrofuran; water / 0.33 h / 20 °C

8.1: monosodium dihydrogen orthophosphate*xH₂O; 2,3-Dimethyl-2-butene; sodium chlorite / tert-butyl alcohol / 0.33 h / 20 °C

9.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl acetamide / 1.5 h

9.2: 4 h

With 4-methyl-morpholine; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,3-Dimethyl-2-butene; monosodium dihydrogen orthophosphate*xH₂O; 2,2'-azobis(isobutyronitrile); hydrogen bromide; sodium hydride; propionic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; phenol; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; N,N-dimethyl acetamide; water; mineral oil; tert-butyl alcohol;

Reference yield:

4-bromo-1,2-bis-bromomethyl-benzene (69189-19-1) → tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.02,6]dec-4-yl)ethyl)-2-methoxybenzoate (1618083-60-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 1.5 h / 20 - 60 °C

1.2: 18 h / 20 - 60 °C

2.1: propionic acid; phenol; hydrogen bromide / water / 10 h / Reflux

3.1: N-ethyl-N,N-diisopropylamine / hexane; dichloromethane / 2 h

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride / tetrahydrofuran / 4 h / 72 °C / Inert atmosphere

5.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol / 3 h

6.1: sodium periodate / tetrahydrofuran; water / 0.33 h / 20 °C

7.1: monosodium dihydrogen orthophosphate*xH₂O; 2,3-Dimethyl-2-butene; sodium chlorite / tert-butyl alcohol / 0.33 h / 20 °C

8.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-methyl-morpholine / N,N-dimethyl acetamide / 1.5 h

8.2: 4 h

With 4-methyl-morpholine; sodium chlorite; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,3-Dimethyl-2-butene; monosodium dihydrogen orthophosphate*xH₂O; hydrogen bromide; sodium hydride; propionic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; phenol; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl acetamide; water; mineral oil; tert-butyl alcohol;

upstream raw materials:

4-bromo-o-xylene

4-bromo-1,2-bis-bromomethyl-benzene

2-(p-toluenesulfonyl)-5-bromoisoindoline

5-bromoisoindoline

Downstream raw materials:

tert-butyl 3-((2R)-2-((isoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate

tert-butyl 3-((2R)-[[2-[2-[(Z)-N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]isoindolin-5-yl]acetyl]amino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate