(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

Base Information

Chemical Name:(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate
CAS No.:1401088-98-9
Molecular Formula:C₂₃H₃₅NO₆
Molecular Weight:421.534
Hs Code.:

Synonyms:(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

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Chemical Property of (2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

Chemical Property:

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Technology Process of (2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

There total 6 articles about (2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate 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: 82.0%

: 67-56-1
methanol

: 1401088-95-6
di-tert-butyl [(2R,4S,E)-4-methyl-1-phenylhept-5-en-2-yl]iminodicarbonate

: 1401088-98-9
(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

Guidance literature:: With ozone; sodium hydroxide; In dichloromethane; at -78 ℃;
DOI:10.1021/jo301693d

Reference yield:

: 1401088-84-3
(S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate

: 1401088-98-9
(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Schlenk technique; Inert atmosphere

1.2: 3 h / -78 - 60 °C / Schlenk technique; Inert atmosphere

2.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Darkness

3.1: 2-methylpropan-2-thiol; triethyl borane / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C / Darkness

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: -78 - 60 °C

5.1: sodium hydroxide; ozone / dichloromethane / -78 °C

With dmap; n-butyllithium; triethyl borane; ozone; 2-methylpropan-2-thiol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; 1.2: |Claisen-Ireland Rearrangement / 3.1: |Barton Decarboxylation;
DOI:10.1021/jo301693d

Reference yield:

: 51871-62-6
(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid

: 1401088-98-9
(2S,4R)-methyl 4-[bis(tert-butoxycarbonyl)amino]-2-methyl-5-phenylpentanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: Novozym 435, an immobilized Candida antarctica lipase (6 weight percent) / 24 h / 20 °C / Enzymatic reaction

1.2: 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 20 °C / Schlenk technique; Inert atmosphere

2.2: 3 h / -78 - 60 °C / Schlenk technique; Inert atmosphere

3.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Darkness

4.1: 2-methylpropan-2-thiol; triethyl borane / tetrahydrofuran; hexane / 1.5 h / 0 - 20 °C / Darkness

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: -78 - 60 °C

6.1: sodium hydroxide; ozone / dichloromethane / -78 °C

With dmap; n-butyllithium; triethyl borane; ozone; 2-methylpropan-2-thiol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; 2.2: |Claisen-Ireland Rearrangement / 4.1: |Barton Decarboxylation;
DOI:10.1021/jo301693d