(2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate

Base Information

• Chemical Name: (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate
• CAS No.: 947682-59-9
• Molecular Formula: C₂₅H₃₇NO₉
• Molecular Weight: 495.57

Synonyms:(2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate

Chemical Property of (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate

There total 7 articles about (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate 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: 88.0%

(2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-((tertbutyldimethylsilyl)oxy)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate (947682-90-8) → (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate (947682-59-9)

Guidance literature:

(2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-((tertbutyldimethylsilyl)oxy)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

With water; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/ol500484f

Reference yield:

N-benzyloxycarbonyl-L-treonine (19728-63-3) → (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate (947682-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

With 1H-imidazole; dmap; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol500484f

Reference yield:

(2S,3S)-tert-butyl 2-(((S)-2-((tert-butyldimethylsilyl)oxy)propanoyl)oxy)-3-methylpentanoate (947682-89-5) → (2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-3-hydroxy-2-((2-oxo-2-phenylethylidene)amino)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate (947682-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine; 2-methyl-6-nitrobenzoic anhydride / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

With dmap; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol500484f

upstream raw materials:

(2S,3S)-tert-butyl 2-(((S)-2-((tert-butyldimethylsilyl)oxy)propanoyl)oxy)-3-methylpentanoate

(2S,3S)-tert-butyl 2-(((S)-2-hydroxypropanoyl)oxy)-3-methylpentanoate

N-benzyloxycarbonyl-L-treonine

(2S,3S)-tert-butyl 2-(((S)-2-(((2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-((tertbutyldimethylsilyl)oxy)butanoyl)oxy)propanoyl)oxy)-3-methylpentanoate

Downstream raw materials:

C₃₇H₅₆N₂O₁₃*C₂HF₃O₂

((2S,5S,8S,13S,16R,17S)-5-((S)-sec-butyl)-8,13-diisobutyl-2,10,10,16-tetramethyl-3,6,9,11,14,18-hexaoxo-1,4,12,15-tetraoxa-7-azacyclooctadecan-17-yl)carbamate

N-((2S,5S,8S,13S,16R,17S)-5-((S)-sec-butyl)-8,13-diisobutyl-2,10,10,16-tetramethyl-3,6,9,11,14,18-hexaoxo-1,4,12,15-tetraoxa-7-azacyclooctadecan-17-yl)-2-hydroxy-3-nitrobenzamide

(S)-(5S,8S,11S,12R,15S)-11-(((benzyloxy)carbonyl)amino)-5-((S)-sec-butyl)-2,2,8,12,17-pentamethyl-4,7,10,14-tetraoxo-3,6,9,13-tetraoxaoctadecan-15-yl 4-((tertbutoxycarbonyl)amino)-2,2,6-trimethyl-3-oxoheptanoate

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