(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Base Information

Chemical Name:(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester
CAS No.:223908-34-7
Molecular Formula:C₂₂H₂₇NO₅
Molecular Weight:385.46
Hs Code.:

Synonyms:(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

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Chemical Property of (4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Chemical Property:

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Technology Process of (4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

There total 8 articles about (4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl 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:

: 55740-07-3
(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 223908-34-7
(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / toluene / 3 h / Heating

2: NaCNBH₃, TMSCl / acetonitrile / 0.5 h / Ambient temperature

With chloro-trimethyl-silane; sodium cyanoborohydride; In toluene; acetonitrile;

Reference yield:

: 220931-41-9
(S)-4-Benzyl-5-[1-ethoxycarbonyl-meth-(E)-ylidene]-oxazolidine-3-carboxylic acid benzyl ester

: 223908-34-7
(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

: 223908-31-4
(3S,4S)-4-(Benzyloxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.5h; Yield given; Yields of byproduct given; Ambient temperature;

Reference yield:

: 112271-08-6
(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

: 223908-34-7
(4S,3R)-4-(benzyloxycarbonyl-methylamino)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / NaBH₄ / ethanol / 2 h / -78 °C

2: 77 percent / p-TsOH / H₂O; toluene / 20 h / Heating

3: 81 percent / TFA, NaBH₃CN / CH₂Cl₂ / 1 h / 0 °C

4: 1.74 g / NaHCO₃ / H₂O; acetone / 16 h / Ambient temperature

With sodium tetrahydroborate; sodium cyanoborohydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; trifluoroacetic acid; In ethanol; dichloromethane; water; acetone; toluene;
DOI:10.1016/S0968-0896(98)00208-9