[(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

Base Information

• Chemical Name: [(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
• CAS No.: 405906-80-1
• Molecular Formula: C₄₀H₃₇BrN₄O₇
• Molecular Weight: 765.66

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(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

There total 18 articles about [(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 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: 86.0%

[(2R,7S,10S)-15-Benzyloxy-4-cyano-2-hydroxymethyl-2-(2-hydroxy-phenyl)-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaen-10-yl]-carbamic acid benzyl ester (405906-79-8) → [(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[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaen-10-yl]-carbamic acid benzyl ester (405906-80-1) + [(2R,7S,10S)-15-Benzyloxy-2-(5-bromo-2-hydroxy-phenyl)-4-cyano-2-hydroxymethyl-7-isopropyl-9-oxo-17-oxa-5,8-diaza-tricyclo[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaen-10-yl]-carbamic acid benzyl ester

Guidance literature:

With t-BuNHBr*HBr; In tetrahydrofuran; dichloromethane; toluene; at -78 - -20 ℃; for 10h;

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

Reference yield:

2'-benzyloxyacetophenone (31165-67-0) → [(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[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaen-10-yl]-carbamic acid benzyl ester (405906-80-1)

Guidance literature:

Multi-step reaction with 12 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

7.1: p-(dimethylamino)pyridine; OsO₄ / tetrahydrofuran

8.1: p-TsOH / toluene / 0.67 h / 95 °C

9.1: 54 percent / dimethylformamide / 20 °C

10.1: NaBH₄; CeCl₃*7H₂O / methanol

11.1: Rieke zinc / tetrahydrofuran; ethanol / 0 °C

12.1: 86 percent / t-BuNHBr*HBr / tetrahydrofuran; toluene; CH₂Cl₂ / 10 h / -78 - -20 °C

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; zirconocene dichloride; silver orthophosphate; hexachloroethane; t-BuNHBr*HBr; potassium tert-butylate; boron tribromide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; johnphos; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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) → [(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[10.3.1.13,6]heptadeca-1(15),3,5,12(16),13-pentaen-10-yl]-carbamic acid benzyl ester (405906-80-1)

Guidance literature:

Multi-step reaction with 10 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

4: p-(dimethylamino)pyridine; OsO₄ / tetrahydrofuran

5: p-TsOH / toluene / 0.67 h / 95 °C

6: 54 percent / dimethylformamide / 20 °C

7: NaBH₄; CeCl₃*7H₂O / methanol

8: Rieke zinc / tetrahydrofuran; ethanol / 0 °C

9: 86 percent / t-BuNHBr*HBr / tetrahydrofuran; toluene; CH₂Cl₂ / 10 h / -78 - -20 °C

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; silver orthophosphate; t-BuNHBr*HBr; potassium tert-butylate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; johnphos; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

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

upstream raw materials:

[(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

N-(Benzyloxycarbonyloxy)succinimide

2'-benzyloxyacetophenone

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

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