(2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile

Base Information

• Chemical Name: (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile
• CAS No.: 271581-30-7
• Molecular Formula: C₃₉H₃₈N₄O₆
• Molecular Weight: 658.754

Synonyms:(2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile

Chemical Property of (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile

There total 6 articles about (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.1^4,7]octadeca-1⁽¹⁷⁾,4,6,13,15-pentaene-5-carbonitrile 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: 90.0%

[(2R,3R,8S,11S)-16-Benzyloxy-3-(2-benzyloxy-phenyl)-5-cyano-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),4,6,13,15-pentaen-11-yl]-carbamic acid tert-butyl ester (271581-29-4) → (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),4,6,13,15-pentaene-5-carbonitrile (271581-30-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 95 ℃; for 1h;

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) → (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),4,6,13,15-pentaene-5-carbonitrile (271581-30-7)

Guidance literature:

Multi-step reaction with 5 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

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: Hydrolysis;

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) → (2R,3R,8S,11S)-11-Amino-16-benzyloxy-3-(2-benzyloxy-phenyl)-2,3-dihydroxy-8-isopropyl-10-oxo-18-oxa-6,9-diaza-tricyclo[11.3.1.14,7]octadeca-1(17),4,6,13,15-pentaene-5-carbonitrile (271581-30-7)

Guidance literature:

Multi-step reaction with 5 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

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: Hydrolysis;

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

upstream raw materials:

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

(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-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

C₅₂H₅₂N₄O₉

{(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

C₆₉H₇₀N₆O₁₀

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