{(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester
• CAS No.: 405906-74-3
• Molecular Formula: C₃₉H₄₁BrN₄O₆
• Molecular Weight: 741.682

Synonyms:{(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester

Chemical Property of {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-yl}-carbamic acid tert-butyl ester

There total 12 articles about {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁶⁾,2,4,6,13⁽¹⁷⁾,14-hexaen-11-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:

2'-benzyloxyacetophenone (31165-67-0) → {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(16),2,4,6,13(17),14-hexaen-11-yl}-carbamic acid tert-butyl ester (405906-74-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: PPh₃; (Cl₃C)2

2.1: Cp₂ZrCl₂; n-BuLi / tetrahydrofuran / -78 - 20 °C

2.2: 85 percent / Pd(OAc)2; P(o-Tol)3; Ag₃PO₄ / tetrahydrofuran / 8 h / 20 °C

3.1: 100 percent / BBr₃ / CH₂Cl₂ / -78 - -20 °C

4.1: 89 percent / DIPEA; TBTU / dimethylformamide / 20 °C

5.1: 82 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 75 °C

6.1: t-BuOK / tetrahydrofuran / 0 °C

With n-butyllithium; zirconocene dichloride; silver orthophosphate; hexachloroethane; potassium tert-butylate; boron tribromide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; johnphos; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011217)40:24<4765::AID-ANIE4765>3.0.CO;2-1

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(16),2,4,6,13(17),14-hexaen-11-yl}-carbamic acid tert-butyl ester (405906-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / DIPEA; TBTU / dimethylformamide / 20 °C

2: 82 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 75 °C

3: t-BuOK / tetrahydrofuran / 0 °C

With silver orthophosphate; potassium tert-butylate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; johnphos; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011217)40:24<4765::AID-ANIE4765>3.0.CO;2-1

Reference yield:

O4'-Benzyl-3'-iod-L-tyrosin (71400-62-9) → {(Z)-(8S,11S)-16-Benzyloxy-3-[2-(2-bromo-ethoxy)-phenyl]-5-cyano-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(16),2,4,6,13(17),14-hexaen-11-yl}-carbamic acid tert-butyl ester (405906-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / DIPEA; TBTU / dimethylformamide / 20 °C

2: 82 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 75 °C

3: t-BuOK / tetrahydrofuran / 0 °C

With silver orthophosphate; potassium tert-butylate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; johnphos; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20011217)40:24<4765::AID-ANIE4765>3.0.CO;2-1

upstream raw materials:

2-bromoethyl triflate

[(Z)-(8S,11S)-16-Benzyloxy-5-cyano-3-(2-hydroxy-phenyl)-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,2,4,6,13,15-hexaen-11-yl]-carbamic acid tert-butyl ester

2'-benzyloxyacetophenone

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Downstream raw materials:

{(2R,7S,10S)-15-Benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl}-carbamic acid benzyl ester

[(2R,7S,10S)-15-Benzyloxy-2-(3-bromo-2-hydroxy-phenyl)-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl]-carbamic acid benzyl ester

{(2S,7S,10S)-15-Benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl}-carbamic acid benzyl ester

[(2R,7S,10S)-15-Benzyloxy-4-cyano-2-hydroxymethyl-2-(2-hydroxy-phenyl)-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁵⁾,3,5,12⁽¹⁶⁾,13-pentaen-10-yl]-carbamic acid benzyl ester

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