(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

Base Information

Chemical Name:(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one
CAS No.:949490-41-9
Molecular Formula:C₂₂H₂₄N₂O₅
Molecular Weight:396.443
Hs Code.:

Synonyms:(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

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Chemical Property of (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

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Technology Process of (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

There total 6 articles about (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one 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: 90.0%

: 7693-46-1
4-Nitrophenyl chloroformate

: 357278-41-2
(4R,5S)-3-Benzyl-5-((S)-1-benzyloxy-2-hydroxy-ethyl)-4-vinyl-oxazolidin-2-one

: 949490-41-9
(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

Guidance literature:: 4-Nitrophenyl chloroformate; (4R,5S)-3-Benzyl-5-((S)-1-benzyloxy-2-hydroxy-ethyl)-4-vinyl-oxazolidin-2-one; With pyridine; at 20 ℃; for 0.5h;

With ammonia; In methanol; at 0 ℃; for 1h; Further stages.;
DOI:10.1016/j.tetasy.2007.06.002

Reference yield:

: 100-46-9
benzylamine

: 949490-41-9
(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: MS 4 Angstroem / diethyl ether / 3 h / 20 °C

2.1: 64 percent / BF₃*Et₂O / diethyl ether / -78 °C

3.1: 90 percent / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 70 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 3.5 h / 20 °C

5.1: 83 percent / TBAF/SiO₂ / tetrahydrofuran / 20 °C

6.1: pyridine / 0.5 h / 20 °C

6.2: 90 percent / NH₃ / methanol / 1 h / 0 °C

With pyridine; MS 4 Angstroem; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; water;
DOI:10.1016/j.tetasy.2007.06.002

Reference yield:

: 357278-39-8
(4R,5S)-3-benzyl-5-((1S)-2-tert-butyldiphenylsilyloxy-1-hydroxyethyl)-4-vinyl-1,3-oxazolan-2-one

: 949490-41-9
(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 70 percent / tetrabutylammonium iodide; NaH / tetrahydrofuran / 3.5 h / 20 °C

2.1: 83 percent / TBAF/SiO₂ / tetrahydrofuran / 20 °C

3.1: pyridine / 0.5 h / 20 °C

3.2: 90 percent / NH₃ / methanol / 1 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1016/j.tetasy.2007.06.002