{(S)-1-[(2S,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

Base Information

• Chemical Name: {(S)-1-[(2S,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
• CAS No.: 271581-39-6
• Molecular Formula: C₅₂H₅₃N₅O₈
• Molecular Weight: 876.022

Synonyms:{(S)-1-[(2S,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

Chemical Property of {(S)-1-[(2S,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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-1-[(2S,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

There total 10 articles about {(S)-1-[(2S,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 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: 85.0%

{(S)-1-[(2R,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 (271581-36-3) → {(S)-1-[(2S,7S,10S)-15-Benzyloxy-2-(2-benzyloxy-phenyl)-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(16),3,5,12,14-pentaen-10-ylcarbamoyl]-2-methyl-propyl}-carbamic acid benzyl ester (271581-39-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 ℃;

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

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-hydroxymethyl-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 (271581-39-6)

Guidance literature:

Multi-step reaction with 8 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: 90 percent / p-TsOH / toluene / 1 h / 95 °C

6.1: TBTU; DIPEA / dimethylformamide

7.1: p-TsOH / 95 °C

8.1: 85 percent / NaBH₄ / methanol; tetrahydrofuran / -10 °C

With dmap; sodium tetrahydroborate; 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; methanol; 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: Hydrolysis / 6.1: Acylation / 7.1: Rearrangement / 8.1: Reduction;

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-hydroxymethyl-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 (271581-39-6)

Guidance literature:

Multi-step reaction with 8 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: 90 percent / p-TsOH / toluene / 1 h / 95 °C

6.1: TBTU; DIPEA / dimethylformamide

7.1: p-TsOH / 95 °C

8.1: 85 percent / NaBH₄ / methanol; tetrahydrofuran / -10 °C

With dmap; sodium tetrahydroborate; 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; methanol; 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: Hydrolysis / 6.1: Acylation / 7.1: Rearrangement / 8.1: Reduction;

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

upstream raw materials:

{(S)-1-[(2R,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

(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

Downstream raw materials:

C₅₂H₅₂N₄O₉

C₆₉H₇₀N₆O₁₀

C₇₁H₆₈N₆O₁₁

C₇₁H₇₂N₆O₁₁

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