[(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

Base Information

• Chemical Name: [(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
• CAS No.: 218769-41-6
• Molecular Formula: C₃₇H₃₈N₄O₆
• Molecular Weight: 634.732

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

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Technology Process of [(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

There total 14 articles about [(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 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: 82.0%

[(S)-2-(4-Benzyloxy-3-iodo-phenyl)-1-((S)-1-{4-cyano-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazol-2-yl}-2-methyl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (218769-34-7) → [(Z)-(8S,11S)-16-Benzyloxy-5-cyano-3-(2-hydroxy-phenyl)-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),2,4,6,13,15-hexaen-11-yl]-carbamic acid tert-butyl ester (218769-41-6)

Guidance literature:

With silver orthophosphate; johnphos; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; at 75 ℃;

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

Reference yield:

2-((S)-1-Amino-2-methyl-propyl)-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazole-4-carbonitrile (271581-27-2) → [(Z)-(8S,11S)-16-Benzyloxy-5-cyano-3-(2-hydroxy-phenyl)-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),2,4,6,13,15-hexaen-11-yl]-carbamic acid tert-butyl ester (218769-41-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With silver orthophosphate; 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:

(S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (218769-48-3) → [(Z)-(8S,11S)-16-Benzyloxy-5-cyano-3-(2-hydroxy-phenyl)-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),2,4,6,13,15-hexaen-11-yl]-carbamic acid tert-butyl ester (218769-41-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With silver orthophosphate; 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:

[(S)-2-(4-Benzyloxy-3-iodo-phenyl)-1-((S)-1-{4-cyano-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazol-2-yl}-2-methyl-propylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

2'-benzyloxyacetophenone

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

O^4'-Benzyl-3'-iod-L-tyrosin

Downstream raw materials:

[(Z)-(8S,11S)-16-Benzyloxy-3-(2-benzyloxy-phenyl)-5-cyano-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

{(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

(2S,7S,10S)-10-Amino-15-benzyloxy-2-[2-(2-bromo-ethoxy)-phenyl]-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-pentaene-4-carbonitrile

[(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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