2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester
• CAS No.: 1421947-30-9
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.524

Synonyms:2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester

Chemical Property of 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester

Chemical Property:

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Technology Process of 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester

There total 5 articles about 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl 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: 68.0%

2-tert-butoxycarbonylamino-propionic acid 3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-2-trimethylsilanylethynyl-benzyl ester (1421947-26-3) → 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester (1421947-30-9)

Guidance literature:

With methanol; potassium fluoride; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2012.12.064

Reference yield:

3-Methyl-1,2-diiodobenzene (1608-48-6) → 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester (1421947-30-9)

Guidance literature:

Multi-step reaction with 5 steps

1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Inert atmosphere; Reflux

2: potassium carbonate / acetone / 0.5 h / Inert atmosphere; Reflux

3: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 0.5 h / 20 °C / Inert atmosphere

4: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 16 h / 20 °C / Inert atmosphere

5: methanol; potassium fluoride / methanol / 1 h / 20 °C / Inert atmosphere

With methanol; potassium fluoride; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; dibenzoyl peroxide; In methanol; tetrachloromethane; acetone; 3: |Sonogashira Cross-Coupling / 4: |Sonogashira Cross-Coupling;

DOI:10.1016/j.tet.2012.12.064

Reference yield:

1-bromomethyl-2,3-diiodobenzene (1421947-17-2) → 2-tert-butoxycarbonylamino-propionic acid 2-ethynyl-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester (1421947-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / acetone / 0.5 h / Inert atmosphere; Reflux

2: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 0.5 h / 20 °C / Inert atmosphere

3: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 16 h / 20 °C / Inert atmosphere

4: methanol; potassium fluoride / methanol / 1 h / 20 °C / Inert atmosphere

With methanol; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; In methanol; acetone; 2: |Sonogashira Cross-Coupling / 3: |Sonogashira Cross-Coupling;

DOI:10.1016/j.tet.2012.12.064

upstream raw materials:

3-Methyl-1,2-diiodobenzene

1-bromomethyl-2,3-diiodobenzene

C₁₅H₁₉I₂NO₄

2-tert-butoxycarbonylamino-propionic acid 2-iodo-3-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-benzyl ester

Downstream raw materials:

2-tert-butoxycarbonylamino-propionic acid 3-(3-hydroxy-prop-1-ynyl)-2-{4-phenyl-3-[(toluene-4-sulfonylamino)-methyl]-but-3-en-1-ynyl}-benzyl ester

C₃₇H₄₀N₂O₉S₂

C₃₆H₃₆N₂O₆S

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