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

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Chemical Name:(2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoic acid
CAS No.:402925-43-3
Molecular Formula:C₂₉H₃₈N₂O₈
Molecular Weight:542.629
Hs Code.:

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

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

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

There total 7 articles about (2S,3R,1'S)-5-[benzyloxycarbonyl-(1'-methoxycarbonyl-2'-phenylethyl)amino]-2-tert-butoxycarbonylamino-3-methyl-pentanoic 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: 89.0%

: 402925-42-2
(4S,1'R,1''S)-4-{3'-[benzyloxycarbonyl-(1''-methoxycarbonyl-2''-phenylethyl)amino]-1'-methylpropyl}-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

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

Guidance literature:: With jones' reagent; In acetone; at 0 - 20 ℃; for 1h;
DOI:10.1016/S0040-4039(01)01847-0

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / sodium triacetoxyborohydride / tetrahydrofuran / 15 h / 20 °C

2: 85 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

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

With jones reagent; sodium tris(acetoxy)borohydride; sodium carbonate; In tetrahydrofuran; water; acetone; 3: 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

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

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C

2: 96 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 90 percent / sodium triacetoxyborohydride / tetrahydrofuran / 15 h / 20 °C

4: 85 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 1 h / 20 °C

5: 89 percent / Jones reagent / acetone / 3 h / 20 °C

With lithium aluminium tetrahydride; jones reagent; oxalyl dichloride; sodium tris(acetoxy)borohydride; sodium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; 2: Swern oxidation / 5: Jones oxidation;
DOI:10.1021/jo050736k