pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

Base Information

Chemical Name:pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate
CAS No.:862473-12-9
Molecular Formula:C₃₅H₃₇F₅N₂O₈
Molecular Weight:708.679
Hs Code.:

pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

Synonyms:pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

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Chemical Property of pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

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Technology Process of pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

There total 8 articles about pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate 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: 77.0%

: 771-61-9
2,3,4,5,6-pentafluorophenol

: 402925-43-3
(2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoic acid

: 862473-12-9
pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

Guidance literature:: (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoic acid; With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; for 0.166667h;

2,3,4,5,6-pentafluorophenol; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo050736k

Reference yield:

: 2577-90-4
methyl (2S)-2-amino-3-phenylpropanoate

: 862473-12-9
pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / sodium triacetoxyborohydride / tetrahydrofuran / 15 h / 20 °C

2.1: 85 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: 89 percent / Jones reagent / acetone / 3 h / 20 °C

4.1: EDC / CH₂Cl₂ / 0.17 h / 0 °C

4.2: 77 percent / CH₂Cl₂ / 2 h / 20 °C

With jones reagent; sodium tris(acetoxy)borohydride; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; water; acetone; 3.1: Jones oxidation;
DOI:10.1021/jo050736k

Reference yield:

: 131713-28-5
(1'R,4S)-4-(2'-ethoxycarbonyl-1'-methyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 862473-12-9
pentafluorophenyl (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

2.1: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 90 percent / sodium triacetoxyborohydride / tetrahydrofuran / 15 h / 20 °C

4.1: 85 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: 89 percent / Jones reagent / acetone / 3 h / 20 °C

6.1: EDC / CH₂Cl₂ / 0.17 h / 0 °C

6.2: 77 percent / CH₂Cl₂ / 2 h / 20 °C

With lithium aluminium tetrahydride; jones reagent; oxalyl dichloride; sodium tris(acetoxy)borohydride; sodium carbonate; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; 2.1: Swern oxidation / 5.1: Jones oxidation;
DOI:10.1021/jo050736k