(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

Base Information

Chemical Name:(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone
CAS No.:1393834-04-2
Molecular Formula:C₃₉H₃₃NO₄
Molecular Weight:579.695
Hs Code.:

Synonyms:(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

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Chemical Property of (2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

Chemical Property:

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Technology Process of (2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

There total 8 articles about (2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone 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: 65.0%

: (4R,E)-3-(4'-benzyloxybut-2'-enoyl)-4,5,5-triphenyloxazolidinone

: 100-39-0
benzyl bromide

: 1393834-04-2
(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

: 1393834-00-8
(2'R,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

Guidance literature:: (4R,E)-3-(4'-benzyloxybut-2'-enoyl)-4,5,5-triphenyloxazolidinone; With lithium chloride; In tetrahydrofuran; at -60 ℃; for 0.25h; Inert atmosphere;

With potassium hexamethylsilazane; In tetrahydrofuran; at -60 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at -45 ℃; for 7h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2015.05.037

Reference yield:

: C₃₂H₂₇NO₄

: 100-39-0
benzyl bromide

: 1393834-04-2
(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

: 1393834-00-8
(2'R,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

Guidance literature:: C₃₂H₂₇NO₄; With potassium hexamethylsilazane; lithium chloride; In tetrahydrofuran; at -60 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at -60 - -45 ℃; for 7h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Saturated solution;
DOI:10.1016/j.tetlet.2012.06.133

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 1393834-04-2
(2'S,4R,Z)-3-(4'-benzyloxyl-2'-benzylbut-3'-enoyl)-4,5,5-triphenyloxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine; acetic acid / toluene / 18 h / 110 °C

2.1: lithium hydroxide / tetrahydrofuran; water / 18 h / 25 °C

3.1: lithium chloride; triethylamine; pivaloyl chloride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.2: 18 h / 0 - 20 °C / Inert atmosphere

4.1: lithium chloride / tetrahydrofuran / 0.25 h / -60 °C / Inert atmosphere

4.2: 0.5 h / -60 °C / Inert atmosphere

4.3: 7 h / -45 °C / Inert atmosphere

With pivaloyl chloride; acetic acid; triethylamine; triphenylphosphine; lithium chloride; lithium hydroxide; In tetrahydrofuran; water; toluene;
DOI:10.1016/j.tet.2015.05.037