4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

Base Information

Chemical Name:4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate
CAS No.:495401-26-8
Molecular Formula:C₅₀H₆₂N₄O₁₄
Molecular Weight:943.061
Hs Code.:

4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

Synonyms:4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

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Chemical Property of 4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

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Technology Process of 4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

There total 15 articles about 4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate 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: 62.0%

: 495401-25-7
4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-(allyloxycarbonyl)-2-hydroxypentyl]-3-pyridiniumolate

: 495401-26-8
4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline; In tetrahydrofuran; at 20 ℃; for 76h;
DOI:10.1016/S0957-4166(02)00477-9

Reference yield:

: 441353-28-2
allyl (2S,5R)-2-benzyloxycarbonylamino-5-hydroxy-6-iodohexanoate

: 495401-26-8
4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / acetonitrile / 16 h / Heating

2: 60 percent / N-methylaniline; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 76 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-methylaniline; In tetrahydrofuran; acetonitrile;
DOI:10.1016/S0957-4166(03)00400-2

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 495401-26-8
4-[(S)-2-benzyloxycarbonylamino-2-(tert-butyloxycarbonyl)ethyl]-5-[(S)-3-benzyloxycarbonylamino-3-(tert-butyloxycarbonyl)propyl]-1-[(2R,5S)-5-benzyloxycarbonylamino-5-carboxy-2-hydroxypentyl]-3-pyridiniumolate

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / dioxane; H₂O / 2.5 h / 20 °C

2: 98 percent / aq. trifluoroacetic acid / 1 h / 20 °C

3: 39 percent / aq. NaHCO₃; I₂; KI / CH₂Cl₂ / 48 h / 0 °C

4: 82 percent / Cs₂CO₃ / 0.13 h / Heating

5: 65 percent / acetonitrile / 16 h / Heating

6: 60 percent / N-methylaniline; tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 76 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; sodium hydrogencarbonate; caesium carbonate; N-methylaniline; trifluoroacetic acid; potassium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;
DOI:10.1016/S0957-4166(03)00400-2