(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

Base Information

Chemical Name:(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid
CAS No.:357617-27-7
Molecular Formula:C₂₃H₂₂FNO₅
Molecular Weight:411.43
Hs Code.:

Synonyms:(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

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Chemical Property of (2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

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Technology Process of (2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

There total 8 articles about (2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid 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%

: (2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid methyl ester hydrochloride

: 357617-27-7
(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

Guidance literature:: With sodium hydroxide; In methanol; water; at 20 ℃; for 24h;
DOI:10.1021/jo010327y

Reference yield:

: 4248-19-5
tert-butyl carbazate

: (E)-3-(4,5-Bis-benzyloxy-2-fluoro-phenyl)-acrylic acid methyl ester

: 357617-27-7
(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

: (2R,3S)-2-Amino-3-(4,5-bis-benzyloxy-2-fluoro-phenyl)-3-hydroxy-propionic acid

: 3-(4,5-bis-benzyloxy-2-fluoro-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-propionic acid methyl ester

Guidance literature:: tert-butyl carbazate; (E)-3-(4,5-Bis-benzyloxy-2-fluoro-phenyl)-acrylic acid methyl ester; With sodium hydroxide; potassium dioxotetrahydroxoosmate(VI); tert-butylhypochlorite; hydroquinidine anthraquinone-1,4-diyl diether; In propan-1-ol; water; acetonitrile; at 20 ℃; for 2h;

With hydrogenchloride; In ethyl acetate; at 20 ℃; for 4h;

With sodium hydroxide; water; In methanol; at 20 ℃; for 24h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(01)01816-0

Reference yield:

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

: 357617-27-7
(2S,3R)-2-amino-3-[4,5-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

Guidance literature:: Multi-step reaction with 7 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

3: 95 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 87 percent / Hg(OAc)2 / CH₂Cl₂ / 0 - 20 °C

5: 76 percent / Cs₂CO₃ / methanol / 3.5 h / 20 °C

6: 92 percent / HCl / ethyl acetate / 5 h / 20 °C

7: 94 percent / NaOH / methanol; H₂O / 24 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; tin(II) trifluoromethanesulfonate; mercury(II) diacetate; caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo010327y