(2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane

Base Information

• Chemical Name: (2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane
• CAS No.: 134653-34-2
• Molecular Formula: C₃₂H₄₄N₂O₈
• Molecular Weight: 584.71

Synonyms:(2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane

Chemical Property of (2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane

Chemical Property:

Purity/Quality:

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Technology Process of (2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane

There total 4 articles about (2S)-N⁴,N⁴-bis<(benzyloxycarbonyl)methyl>-N²-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane 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:

3,4-dihydro-2H-pyran (110-87-2) → (2S)-N4,N4-bis<(benzyloxycarbonyl)methyl>-N2-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane (134653-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 25 °C

2: piperidine / dimethylformamide / 0.5 h / 25 °C

3: NaHCO₃, NaI / dimethylformamide / 19 h / 25 °C

With piperidine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00014a006

Reference yield:

(2S)-N2-Boc-N4-Fmoc-2,4-diamino-1-butanol (134653-33-1) → (2S)-N4,N4-bis<(benzyloxycarbonyl)methyl>-N2-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane (134653-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 25 °C

2: piperidine / dimethylformamide / 0.5 h / 25 °C

3: NaHCO₃, NaI / dimethylformamide / 19 h / 25 °C

With piperidine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00014a006

Reference yield:

Nα-t-Boc-Nγ-(9-fluorenylmethyloxycarbonyl)-(L)-2,4-diaminobutyric acid (117106-21-5,131570-57-5) → (2S)-N4,N4-bis<(benzyloxycarbonyl)methyl>-N2-Boc-1-(2'-tetrahydropyranyloxy)-2,4-diaminobutane (134653-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) ClCO₂Et, Et₃N, 2.) NaBH₄ / 1.) THF, -5 deg C, 0.5 h, 2.) H₂O, 0 deg C, 4 h

2: 0.45 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 25 °C

3: piperidine / dimethylformamide / 0.5 h / 25 °C

4: NaHCO₃, NaI / dimethylformamide / 19 h / 25 °C

With piperidine; sodium tetrahydroborate; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00014a006

upstream raw materials:

3,4-dihydro-2H-pyran

(2S)-N²-Boc-N⁴-Fmoc-2,4-diamino-1-butanol

N^α-t-Boc-N^γ-(9-fluorenylmethyloxycarbonyl)-(L)-2,4-diaminobutyric acid

Downstream raw materials:

Boc-Ada²(Bzl₂)

Boc-Ada²(Bzl₂)-Ala p-nitrobenzyl ester

Boc-Ada²-Ala(Bzl₂)

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