(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

Base Information

Chemical Name:(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine
CAS No.:119719-83-4
Molecular Formula:C₂₇H₃₀N₂O₆S
Molecular Weight:510.611
Hs Code.:

Synonyms:(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

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Chemical Property of (3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

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Technology Process of (3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

There total 15 articles about (3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>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: 84.0%

: 103321-68-2
(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-(hydroxymethyl)isoxazolidine

: 98-59-9
p-toluenesulfonyl chloride

: 119719-83-4
(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 10h; Ambient temperature;
DOI:10.1021/jo00270a037

Reference yield:

: 5041-33-8
N-(Benzyloxycarbonyl)allylamine

: 119719-83-4
(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: toluene, reflux, 14 h

2: 10 percent HCl, MeOH / 4 h / 90 °C

3: K₂CO₃ / dimethylformamide / 1 h / 50 °C

4: LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

5: (iPr)2NEt, Et₃N / CH₂Cl₂ / 10 h / 0 - 25 °C

With hydrogenchloride; methanol; lithium aluminium tetrahydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00275a064

Reference yield:

: 100-39-0
benzyl bromide

: 119719-83-4
(3S,5R)-N-benzyl-5-<<(benzyloxycarbonyl)amino>methyl>-3-<<(p-tolylsulfonyl)oxy>methyl>isoxazolidine

Guidance literature:: Multi-step reaction with 3 steps

1: K₂CO₃ / dimethylformamide / 1 h / 50 °C

2: LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

3: (iPr)2NEt, Et₃N / CH₂Cl₂ / 10 h / 0 - 25 °C

With lithium aluminium tetrahydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00275a064