(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

Base Information

Chemical Name:(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester
CAS No.:186758-19-0
Molecular Formula:C₁₅H₂₀FNO₅
Molecular Weight:313.326
Hs Code.:

Synonyms:(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

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Chemical Property of (2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

Chemical Property:

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Technology Process of (2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

There total 6 articles about (2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic 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: 94.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 186758-18-9
(2R,3S)-3-Azido-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

: 186758-19-0
(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3.5h; under 760 Torr; Ambient temperature;
DOI:10.3987/com-96-s20

Reference yield:

: 74325-03-4
methyl (E)-m-fluorocinnamate

: 186758-19-0
(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 67 percent / K₃Fe(CN)6, K₂CO₃, (DHQ)2PHAL, osmium tetroxide / 2-methyl-propan-2-ol; H₂O / 18 h / Ambient temperature

2: p-TsOH*H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

3: CH₂Cl₂ / -15 deg C, 1 h then 0 deg C, 2 h

4: 67 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C

5: 91 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

6: 94 percent / H₂ / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature

With osmium(VIII) oxide; sodium azide; Hydroquinone 1,4-phthalazinediyl diether; hydrogen; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.3987/com-96-s20

Reference yield:

: 186758-26-9
(2R,3S)-3-(3-Fluoro-phenyl)-2,3-dihydroxy-propionic acid methyl ester

: 186758-19-0
(2R,3S)-3-tert-Butoxycarbonylamino-3-(3-fluoro-phenyl)-2-hydroxy-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: p-TsOH*H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

2: CH₂Cl₂ / -15 deg C, 1 h then 0 deg C, 2 h

3: 67 percent / sodium azide / dimethylformamide / 2.5 h / 40 °C

4: 91 percent / K₂CO₃ / methanol / 0.33 h / 0 °C

5: 94 percent / H₂ / Pd/C / ethyl acetate / 3.5 h / 760 Torr / Ambient temperature

With sodium azide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.3987/com-96-s20