N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

Base Information

Chemical Name:N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester
CAS No.:81926-51-4
Molecular Formula:C₁₆H₂₃NO₅
Molecular Weight:309.362
Hs Code.:

Synonyms:N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

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Chemical Property of N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

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Technology Process of N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

There total 16 articles about N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic 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: 95.0%

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

: 172025-60-4
(2S,3R)-3-Azido-2-hydroxy-4-phenyl-butyric acid methyl ester

: 81926-51-4
N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 5h;
DOI:10.1016/S0040-4039(03)01799-4

Reference yield: 39.0%

: 1334163-98-2
C₂₂H₃₄N₂O₇

: 124-41-4
sodium methylate

: 81926-51-4
N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

Guidance literature:: C₂₂H₃₄N₂O₇; With trifluoroacetic acid; In dichloromethane; for 0.166667h; Inert atmosphere;

With hydrogen; In ethanol; for 12h;

sodium methylate; optical yield given as %ee; Further stages;
DOI:10.1002/chem.201101076

Reference yield:

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 81926-51-4
N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: {2,2-bis[(4R)-Ph-oxazoline-2-yl]propane}*Cu(OTf)2 / CH₂Cl₂ / 20 °C

2: L-Selectride / CH₂Cl₂ / 1 h / -78 °C

3: H₂ / Raney-Ni / methanol

4: DMAP

5: NaOMe

With dmap; [Cu(OTf)2((R)-Ph-BOX)]; hydrogen; sodium methylate; L-Selectride; nickel; In methanol; dichloromethane;
DOI:10.1021/ja0175486