{[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester

Base Information

• Chemical Name: {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester
• CAS No.: 869110-69-0
• Molecular Formula: C₄₀H₆₀N₂O₉
• Molecular Weight: 712.924

Synonyms:{[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester

Chemical Property of {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester

Chemical Property:

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Technology Process of {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester

There total 6 articles about {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester 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:

2-amino-3-(4-benzyloxyphenyl)propionamide (73504-43-5) → {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester (869110-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: BH₃*THF / tetrahydrofuran / 7 h / Heating

2: 2.2 g / NaI; proton sponge / acetonitrile / 13 h / Heating

With borane-THF; Proton Sponge; sodium iodide; In tetrahydrofuran; acetonitrile;

DOI:10.1039/b507917a

Reference yield:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester (869110-69-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium carbonate; potassium iodide / acetonitrile / 6 h / 90 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 50 °C

3.1: isobutyl chloroformate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

3.2: 24 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C

5.1: borane-THF / tetrahydrofuran / 24 h / Reflux

6.1: N-ethyl-N,N-diisopropylamine; potassium iodide / acetonitrile / Heating

With borane-THF; water; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; sodium hydroxide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/acs.jmedchem.1c00393

Reference yield:

N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester (27513-44-6) → {[1-(4-benzyloxy-benzyl)-2-(bis-tert-butoxycarbonylmethyl-amino)-ethyl]-tert-butoxycarbonylmethyl-amino}-acetic acid tert-butyl ester (869110-69-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide; water / tetrahydrofuran / 1 h / 50 °C

2.1: isobutyl chloroformate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

2.2: 24 h / 20 °C

3.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C

4.1: borane-THF / tetrahydrofuran / 24 h / Reflux

5.1: N-ethyl-N,N-diisopropylamine; potassium iodide / acetonitrile / Heating

With borane-THF; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; potassium iodide; sodium hydroxide; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/acs.jmedchem.1c00393

upstream raw materials:

2-amino-3-(4-benzyloxyphenyl)propionamide

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

benzyl chloride

N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

Downstream raw materials:

Hexadecanoic acid (R)-2-(benzyloxy-{4-[(S)-2,3-bis-(bis-tert-butoxycarbonylmethyl-amino)-propyl]-phenoxy}-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-2-(benzyloxy-{4-[(S)-2,3-bis-(bis-tert-butoxycarbonylmethyl-amino)-propyl]-phenoxy}-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-2-({4-[(S)-2,3-bis-(bis-tert-butoxycarbonylmethyl-amino)-propyl]-phenoxy}-hydroxy-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-2-({4-[(S)-2,3-bis-(bis-carboxymethyl-amino)-propyl]-phenoxy}-hydroxy-phosphoryloxy)-1-hexadecanoyloxymethyl-ethyl ester

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