benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester
• CAS No.: 575452-21-0
• Molecular Formula: C₄₅H₅₅NO₁₀
• Molecular Weight: 769.932

Synonyms:benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester

Chemical Property of benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester

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Technology Process of benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester

There total 4 articles about benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic 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: 66.0%

3-formyl-dibenzo[24]crown-8 (209855-90-3) + {4-[(benzyl-tert-butoxycarbonyl-amino)-methyl]-benzyl}-triphenyl-phosphonium; iodide → benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.012,17]dotriaconta-1(28),12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester (575452-21-0)

Guidance literature:

{4-[(benzyl-tert-butoxycarbonyl-amino)-methyl]-benzyl}-triphenyl-phosphonium; iodide; With sodium hydride; In dichloromethane; at 20 ℃; for 0.5h;

3-formyl-dibenzo[24]crown-8; In dichloromethane; for 20h;

DOI:10.1002/anie.200390296

Reference yield:

N-(tert-butoxycarbonyl)-N-benzyl-4-(hydroxymethyl)benzylamine (199982-19-9) → benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.012,17]dotriaconta-1(28),12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester (575452-21-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 78 percent / N-chlorosuccinimide; PPh₃ / tetrahydrofuran / 20 °C

2.1: 95 percent / NaI / acetone / 20 °C

3.1: 88 percent / benzene / 2 h / Heating

4.1: NaH / CH₂Cl₂ / 0.5 h / 20 °C

4.2: 66 percent / CH₂Cl₂ / 20 h

With N-chloro-succinimide; sodium hydride; triphenylphosphine; sodium iodide; In tetrahydrofuran; dichloromethane; acetone; benzene; 2.1: Finkelstein reaction / 4.2: Wittig reaction;

DOI:10.1002/anie.200390296

Reference yield:

benzyl-(4-chloromethyl-benzyl)-carbamic acid tert-butyl ester (575452-18-5) → benzyl-{4-[2-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.012,17]dotriaconta-1(28),12,14,16,29,31-hexaen-14-yl)-vinyl]-benzyl}-carbamic acid tert-butyl ester (575452-21-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / NaI / acetone / 20 °C

2.1: 88 percent / benzene / 2 h / Heating

3.1: NaH / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 66 percent / CH₂Cl₂ / 20 h

With sodium hydride; sodium iodide; In dichloromethane; acetone; benzene; 1.1: Finkelstein reaction / 3.2: Wittig reaction;

DOI:10.1002/anie.200390296

upstream raw materials:

3-formyl-dibenzo[24]crown-8

N-(tert-butoxycarbonyl)-N-benzyl-4-(hydroxymethyl)benzylamine

benzyl-(4-chloromethyl-benzyl)-carbamic acid tert-butyl ester

benzyl-(4-iodomethyl-benzyl)-carbamic acid tert-butyl ester

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