(3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine

Base Information

• Chemical Name: (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine
• CAS No.: 1392303-10-4
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4

Synonyms:(3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine

Chemical Property of (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine

There total 5 articles about (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine 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:

methanol (67-56-1) + carbon monoxide (201230-82-2) + (1R,2S)-(+)-tert-butyl [(1-phenyl-2-methyl-3-butene-1-yl)oxy]carbamate (1392302-99-6) → (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-10-4) + (3S,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-11-5)

Guidance literature:

carbon monoxide; With copper diacetate; palladium dichloride; In methyl orthoacetate; at 20 ℃; for 0.5h;

methanol; (1R,2S)-(+)-tert-butyl [(1-phenyl-2-methyl-3-butene-1-yl)oxy]carbamate; at 40 ℃; optical yield given as %de;

DOI:10.1002/chem.201102716

Reference yield:

C19H17NO3 → (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-10-4) + (3S,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / dichloromethane; water / 24 h / 20 °C / Inert atmosphere

3.1: copper diacetate; palladium dichloride / methyl orthoacetate / 0.5 h / 20 °C

3.2: 40 °C

With copper diacetate; hydrazine hydrate; sodium hydroxide; palladium dichloride; In tetrahydrofuran; dichloromethane; methyl orthoacetate; water;

DOI:10.1002/chem.201102716

Reference yield:

(1S,2S)-2-methyl-1-phenyl-3-buten-1-ol (25201-44-9,52922-10-8,52922-19-7,63553-62-8,63553-63-9,103882-39-9,121842-16-8,122332-13-2,103882-41-3) → (3R,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-10-4) + (3S,4S,5R)-(+)-N-tert-butoxycarbonyl-3-(methoxycarbonylmethyl)-4-methyl-5-phenylisoxazolidine (1392303-11-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triphenylphosphine / tetrahydrofuran / 0.03 h / 0 °C / Inert atmosphere

1.2: 2.5 h / 20 °C / Inert atmosphere

2.1: hydrazine hydrate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / dichloromethane; water / 24 h / 20 °C / Inert atmosphere

4.1: copper diacetate; palladium dichloride / methyl orthoacetate / 0.5 h / 20 °C

4.2: 40 °C

With copper diacetate; hydrazine hydrate; triphenylphosphine; sodium hydroxide; palladium dichloride; In tetrahydrofuran; dichloromethane; methyl orthoacetate; water; 1.1: Mitsunobu reaction / 1.2: Mitsunobu reaction;

DOI:10.1002/chem.201102716

upstream raw materials:

methanol

carbon monoxide

(1R,2S)-(+)-tert-butyl [(1-phenyl-2-methyl-3-butene-1-yl)oxy]carbamate

(1R,2S)-(+)-O-[1-phenyl-2-methyl-3-butene-1-yl]hydroxylamine

Downstream raw materials:

methyl (3S,5R)-(+)-3-(tert-butoxycarbamoyl)-5-hydroxy-3-methyl-5-(phenyl)valerate

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