(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

Base Information

Chemical Name:(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester
CAS No.:357617-17-5
Molecular Formula:C₂₅H₂₂FNO₅S
Molecular Weight:467.518
Hs Code.:

Synonyms:(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

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Chemical Property of (4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

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Technology Process of (4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

There total 2 articles about (4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester 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: 93.0%

: methoxymagnesium bromide

: 357617-15-3
(4S)-4-benzyl-3-[(4S,5R)-1-[5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidin-4-yl]methanoyl]oxazolidin-2-one

: 357617-17-5
(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

Guidance literature:: In tetrahydrofuran; methanol; at 0 ℃; for 0.583333h;
DOI:10.1021/jo010327y

Reference yield:

: 71924-67-9
4,5-bis(benzyloxy)-2-fluorobenzaldehyde

: 357617-17-5
(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / lithium hexamethyldisilazane; Sn(OTf)2 / tetrahydrofuran / 1.5 h / -78 °C

2: 93 percent / tetrahydrofuran; methanol / 0.58 h / 0 °C

With tin(II) trifluoromethanesulfonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol;
DOI:10.1021/jo010327y

Reference yield:

: 357617-17-5
(4S,5R)-5-[4,5-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

: (2S,3R)-3-(4,5-dihydroxy-2-fluorophenyl)serine

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 87 percent / Hg(OAc)2 / CH₂Cl₂ / 0 - 20 °C

3: 76 percent / Cs₂CO₃ / methanol / 3.5 h / 20 °C

4: 92 percent / HCl / ethyl acetate / 5 h / 20 °C

5: 94 percent / NaOH / methanol; H₂O / 24 h / 20 °C

6: 80 percent / H₂; HCl / Pd-C / methanol; H₂O / 2 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; mercury(II) diacetate; hydrogen; caesium carbonate; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo010327y