{(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester
• CAS No.: 271581-31-8
• Molecular Formula: C₅₂H₅₁N₅O₈
• Molecular Weight: 874.006

Synonyms:{(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Chemical Property of {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

There total 7 articles about {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl 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:

(S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (218769-48-3) → {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(16),3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (271581-31-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / TBTU; DIPEA / dimethylformamide / 20 °C

2.1: 69 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 90 °C

3.1: 97 percent / DEAD; PPh₃ / tetrahydrofuran

4.1: aq. OsO₄; DMAP / 2-methyl-propan-2-ol / 20 °C

4.2: H₂S / tetrahydrofuran / -50 °C

5.1: p-TsOH / toluene / 2.2 h / 95 °C

6.1: 14.6 mg / TBTU; DIPEA / dimethylformamide / 0.67 h / 0 - 20 °C

With dmap; osmium(VIII) oxide; silver orthophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; johnphos; diethylazodicarboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Acylation / 2.1: Dehydroiodination / 3.1: Etherification / 4.1: Oxidation / 4.2: Substitution / 5.1: Rearrangement / 6.1: Acylation;

DOI:10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO;2-A

Reference yield:

2-((S)-1-Amino-2-methyl-propyl)-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazole-4-carbonitrile (271581-27-2) → {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(16),3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (271581-31-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / TBTU; DIPEA / dimethylformamide / 20 °C

2.1: 69 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 90 °C

3.1: 97 percent / DEAD; PPh₃ / tetrahydrofuran

4.1: aq. OsO₄; DMAP / 2-methyl-propan-2-ol / 20 °C

4.2: H₂S / tetrahydrofuran / -50 °C

5.1: p-TsOH / toluene / 2.2 h / 95 °C

6.1: 14.6 mg / TBTU; DIPEA / dimethylformamide / 0.67 h / 0 - 20 °C

With dmap; osmium(VIII) oxide; silver orthophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; johnphos; diethylazodicarboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Acylation / 2.1: Dehydroiodination / 3.1: Etherification / 4.1: Oxidation / 4.2: Substitution / 5.1: Rearrangement / 6.1: Acylation;

DOI:10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO;2-A

Reference yield:

[(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) → {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-formyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(16),3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (271581-31-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 69 percent / 2-(di-tert-butylphosphanyl)biphenyl; Ag₃PO₄ / Pd₂(dba)3 / tetrahydrofuran / 90 °C

2.1: 97 percent / DEAD; PPh₃ / tetrahydrofuran

3.1: aq. OsO₄; DMAP / 2-methyl-propan-2-ol / 20 °C

3.2: H₂S / tetrahydrofuran / -50 °C

4.1: p-TsOH / toluene / 2.2 h / 95 °C

5.1: 14.6 mg / TBTU; DIPEA / dimethylformamide / 0.67 h / 0 - 20 °C

With dmap; osmium(VIII) oxide; silver orthophosphate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; johnphos; diethylazodicarboxylate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Dehydroiodination / 2.1: Etherification / 3.1: Oxidation / 3.2: Substitution / 4.1: Rearrangement / 5.1: Acylation;

DOI:10.1002/(SICI)1521-3773(20000303)39:5<937::AID-ANIE937>3.0.CO;2-A

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

(S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid

2-((S)-1-Amino-2-methyl-propyl)-5-[1-(2-hydroxy-phenyl)-vinyl]-oxazole-4-carbonitrile

[(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

Downstream raw materials:

{(S)-1-[(2R,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.1^3,6]heptadeca-1⁽¹⁶⁾,3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester

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