(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

Base Information

Chemical Name:(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine
CAS No.:143006-56-8
Molecular Formula:C₂₁H₃₀ClNO₃
Molecular Weight:379.927
Hs Code.:

Synonyms:(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

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Chemical Property of (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

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Technology Process of (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

There total 3 articles about (4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine 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%

: 143006-54-6
(4S,5S)-5-((tert-butoxycarbonyl)amino)-2-(chloromethyl)-6-phenyl-1-hexen-4-ol

: 77-76-9
2,2-dimethoxy-propane

: 143006-56-8
(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: With toluene-4-sulfonic acid; for 46h; Ambient temperature;
DOI:10.1021/jo00045a045 DOI:10.1021/jo00093a006

Reference yield:

: 72155-45-4
Boc-L-phenylalaninal

: 143006-56-8
(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 72 percent / BF₃*Et₂O / CHCl₃ / 5 h / -60 °C

2: 84 percent / p-TsOH / 46 h / Ambient temperature

With boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In chloroform;
DOI:10.1021/jo00093a006

Reference yield:

: 161758-23-2
(4S,5S)-5-((tert-Butoxycarbonyl)amino)-1-chloro-6-phenyl-2-((trimethylsilyl)methyl)-1-hexen-4-ol

: 143006-56-8
(4S,5S)-4-benzyl-3-(tert-butoxycarbonyl)-5-(2-(chloromethyl)-3-propenyl)-2,2-dimethyl-1,3-oxazolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

2: 84 percent / p-TsOH / 46 h / Ambient temperature

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran;
DOI:10.1021/jo00093a006