(1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

Base Information

• Chemical Name: (1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine
• CAS No.: 123054-19-3
• Molecular Formula: C₂₁H₃₆N₂O₃
• Molecular Weight: 364.528

Synonyms:(1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

Chemical Property of (1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

Chemical Property:

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Technology Process of (1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

There total 9 articles about (1'S,2S,3S)-N²-(tertbutoxycarbonyl)-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine 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: 81.0%

di-tert-butyl dicarbonate (24424-99-5) + (1'S,2S,3S)-N2,N2,N3-tribenzyl-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-06-8) → (1'S,2S,3S)-N2-(tertbutoxycarbonyl)-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-19-3)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 4h; under 3040 Torr; Ambient temperature;

DOI:10.1021/jo00284a032

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (1'R,2S,3S)-N2, N2, N3-tribenzyl-N3-<1'-9hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123122-71-4) → [(1S,2S)-1-Benzyl-2-((R)-1-hydroxymethyl-2-methyl-propylamino)-butyl]-carbamic acid tert-butyl ester (123054-19-3,123122-72-5)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; for 4h; under 3040 Torr; Ambient temperature;

DOI:10.1021/jo00284a032

Reference yield:

(S)-valinol (2026-48-4,473-75-6) → (1'S,2S,3S)-N2-(tertbutoxycarbonyl)-N3-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine (123054-19-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / acetic acid (pH ca. 6), sodium cyanoborohydride / methanol / 16 h / Ambient temperature

2: 75 percent / neat (no solvent) / 16 h / 50 °C

3: diethyl ether / 1.5 h / 0 - 20 °C

4: 81 percent / H₂ / 20percent Pd(OH)2/C / methanol / 4 h / 3040 Torr / Ambient temperature

With hydrogen; sodium cyanoborohydride; acetic acid; palladium dihydroxide; In methanol; diethyl ether;

DOI:10.1021/jo00284a032

upstream raw materials:

di-tert-butyl dicarbonate

(1'S,2S,3S)-N²,N²,N³-tribenzyl-N³-<1'-(hydroxymethyl)-2'-methylpropyl>-1-phenyl-2,3-pentanediamine

(S)-valinol

(2S)-N,N-dibenzylphenylalaninal

Downstream raw materials:

Boc-PheΨVal-OMe

Boc-PheΨVal-Phe-OMe

Boc-PheΨ(R)Val-Phe-OMe

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