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

Base Information

Chemical Name:(2S,3R)-2-amino-3-[3,4-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid
CAS No.:357617-26-6
Molecular Formula:C₂₃H₂₂FNO₅
Molecular Weight:411.43
Hs Code.:

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

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

Chemical Property:

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

There total 7 articles about (2S,3R)-2-amino-3-[3,4-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: 96.0%

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

: 357617-26-6
(2S,3R)-2-amino-3-[3,4-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:

: 61338-96-3
3,4-bis(benzyloxy)-2-fluorobenzaldehyde

: 357617-26-6
(2S,3R)-2-amino-3-[3,4-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / lithium hexamethyldisilazane; Sn(OTf)2 / tetrahydrofuran / 1.5 h / -78 °C

2: 88 percent / tetrahydrofuran; methanol / 0.33 h / 0 °C

3: 86 percent / DMAP / CH₂Cl₂ / 0.67 h / 20 °C

4: 96 percent / Hg(OAc)2 / CH₂Cl₂ / 0 - 20 °C

5: 83 percent / Cs₂CO₃ / methanol / 3.5 h / 20 °C

6: 72 percent / HCl / ethyl acetate / 5 h / 20 °C

7: 96 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

Reference yield:

: 357617-16-4
(4S,5R)-5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester

: 357617-26-6
(2S,3R)-2-amino-3-[3,4-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / DMAP / CH₂Cl₂ / 0.67 h / 20 °C

2: 96 percent / Hg(OAc)2 / CH₂Cl₂ / 0 - 20 °C

3: 83 percent / Cs₂CO₃ / methanol / 3.5 h / 20 °C

4: 72 percent / HCl / ethyl acetate / 5 h / 20 °C

5: 96 percent / NaOH / methanol; H₂O / 24 h / 20 °C

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