(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

Base Information

Chemical Name:(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate
CAS No.:1597416-69-7
Molecular Formula:C₃₅H₄₀N₂O₇Si
Molecular Weight:628.797
Hs Code.:

Synonyms:(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

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Chemical Property of (S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

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Technology Process of (S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

There total 5 articles about (S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate 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: 60.0%

: 1597416-66-4
(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-iodobenzoate

: 1066-54-2
trimethylsilylacetylene

: 1597416-69-7
(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 60 ℃; for 16h; Inert atmosphere;
DOI:10.1002/anie.201309353

Reference yield:

: 1597416-65-3
phenyl 3-amino-2-iodobenzoate

: 1597416-69-7
(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dicyclohexyl-carbodiimide / tetrahydrofuran / 16.25 h / -10 - 60 °C / Inert atmosphere

2: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201309353

Reference yield:

: 5398-69-6
2-iodo-3-nitrobenzoic acid

: 1597416-69-7
(S)-phenyl 3-(2-(((benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanamido)-2-((trimethylsilyl)ethynyl)benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.2: 2 h / Inert atmosphere

3.1: tin(II) chloride dihdyrate / ethyl acetate / 4 h / Inert atmosphere

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; dicyclohexyl-carbodiimide / tetrahydrofuran / 16.25 h / -10 - 60 °C / Inert atmosphere

5.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; tin(II) chloride dihdyrate; sodium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5.1: |Sonogashira Cross-Coupling;
DOI:10.1002/anie.201309353