(4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide

Base Information

• Chemical Name: (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide
• CAS No.: 1647153-58-9
• Molecular Formula: C₂₄H₃₈N₂O₆
• Molecular Weight: 450.576

Synonyms:(4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide

Chemical Property of (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide

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Technology Process of (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide

There total 6 articles about (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide 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: 77.0%

aminopropane diethyl acetal (41365-75-7) + (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid (1647153-57-8) → (4S,5S)-N2-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide (1647153-58-9)

Guidance literature:

(4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

aminopropane diethyl acetal; With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.3762/bjoc.10.113

Reference yield:

(4R,5S)-N-(benzyloxycarbonyl)-4-(hydroxymethyl)-5-isopropyl-2,2-dimethyloxazolidine (1647153-56-7) → (4S,5S)-N2-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide (1647153-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ruthenium trichloride; sodium periodate / water; tetrachloromethane; acetonitrile / 5 h / 0 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 16 h / 20 °C

With ruthenium trichloride; sodium periodate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.3762/bjoc.10.113

Reference yield:

(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine (1647153-55-6) → (4S,5S)-N2-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide (1647153-58-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 20 °C

2.1: ruthenium trichloride; sodium periodate / water; tetrachloromethane; acetonitrile / 5 h / 0 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.2: 16 h / 20 °C

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.3762/bjoc.10.113

upstream raw materials:

(2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol

(4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

(4R,5S)-N-(benzyloxycarbonyl)-4-(hydroxymethyl)-5-isopropyl-2,2-dimethyloxazolidine

aminopropane diethyl acetal

Downstream raw materials:

(4S,5S)-N²-(benzyloxycarbonyl)-N-(3'-oxopropyl)-3-hydroxyleucine amide

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