(3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

Base Information

Chemical Name:(3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine
CAS No.:1392303-15-9
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

Synonyms:(3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

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Chemical Property of (3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

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Technology Process of (3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

There total 2 articles about (3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine 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: 71.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 1392303-02-4
(S)-(-)-tert-butyl {[2-methyl-1-phenyl-3-buten-1-yl]oxy}carbamate

: 1392303-15-9
(3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

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

methanol; (S)-(-)-tert-butyl {[2-methyl-1-phenyl-3-buten-1-yl]oxy}carbamate; at 40 ℃; optical yield given as %de;
DOI:10.1002/chem.201102716

Reference yield:

: 100-52-7
benzaldehyde

: 1392303-15-9
(3S,4S,5S)-(+)-N-tert-butoxycarbonyl-3-(Methoxycarbonylmethyl)-4-methyl-5-phenyl-isoxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: (+)-5-(2’,4’,6’-trimethoxyphenyl)-8,10,10-trimethyl-6-azatricyclo[7.1.1.02,7]undeca-2,4,6-triene 6-oxide; N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / -40 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 18-crown-6 ether; potassium hydride / hexane / 1 h / 20 °C / Inert atmosphere

2.2: 2 h / -40 - 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 (+)-5-(2’,4’,6’-trimethoxyphenyl)-8,10,10-trimethyl-6-azatricyclo[7.1.1.02,7]undeca-2,4,6-triene 6-oxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 18-crown-6 ether; copper diacetate; potassium hydride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; palladium dichloride; In hexane; dichloromethane; methyl orthoacetate; water; acetonitrile;
DOI:10.1002/chem.201102716