(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

Base Information

Chemical Name:(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone
CAS No.:179927-67-4
Molecular Formula:C₂₂H₂₂FNO₄
Molecular Weight:383.419
Hs Code.:

Synonyms:(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

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Technology Process of (4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

There total 11 articles about (4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone 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: 76.0%

: 179927-66-3
(4R,5S)-(+)-(5-benzyloxy-2-(Z)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

: 179927-67-4
(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: With N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1016/0040-4039(96)00825-8

Reference yield:

: 295330-00-6
(4R,5S)-(+)-(5-benzyloxy-2-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

: 179927-67-4
(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

: (4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(Z)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(00)00444-0

Reference yield:

: 4799-68-2
3-benzyloxypropan-1-ol

: 179927-67-4
(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 81 percent / NaH / benzene / 1 h / 0 °C

3: 97 percent / LiOH / acetone; H₂O / 1 h / 20 °C

4: 2.8 g / SOCl₂ / 1 h

5: 78 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -78 °C

6: LiHMDS; NFOBS / hexane; tetrahydrofuran / 3 h / -78 °C

With lithium hydroxide; n-butyllithium; thionyl chloride; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; acetone; benzene; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: Chlorination / 5: Substitution / 6: Fluorination;
DOI:10.1016/S0040-4020(00)00444-0