(5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene

Base Information

• Chemical Name: (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene
• CAS No.: 548485-10-5
• Molecular Formula: C₃₂H₃₉NO₁₀
• Molecular Weight: 597.662

Synonyms:(5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene

Chemical Property of (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene

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Technology Process of (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene

There total 12 articles about (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene 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: 34.0%

(5S,19S)-27-hydroxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene (548485-24-1) → (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene (548485-10-5)

Guidance literature:

With nitric acid; sodium nitrite;

DOI:10.1016/S0040-4039(02)02030-0

Reference yield:

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) → (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene (548485-10-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 36 percent / NaH / tetrahydrofuran / 60 °C

2.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

2.2: 62 percent / H₂O / tetrahydrofuran; hexane / -78 °C

3.1: 86 percent / EtSNa / dimethylformamide / 80 °C

4.1: 34 percent / aq. NaNO₂; 0.3N HNO₃ / CHCl₃ / 20 °C

With n-butyllithium; nitric acid; sodium hydride; sodium nitrite; sodium thioethylate; In tetrahydrofuran; hexane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(03)00031-4

Reference yield:

(5S,19S)-25-bromo-27-methoxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene (548485-22-9) → (5S,19S)-27-hydroxy-25-nitro-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1(26),23(27),24-triene (548485-10-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

1.2: 62 percent / H₂O / tetrahydrofuran; hexane / -78 °C

2.1: 86 percent / EtSNa / dimethylformamide / 80 °C

3.1: 34 percent / aq. NaNO₂; 0.3N HNO₃ / CHCl₃ / 20 °C

With n-butyllithium; nitric acid; sodium nitrite; sodium thioethylate; In tetrahydrofuran; hexane; chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(03)00031-4

upstream raw materials:

(5S,19S)-27-hydroxy-5,19-diphenyl-3,6,9,12,15,18,21-heptaoxabicyclo[21.3.1]heptacosa-1⁽²⁶⁾,23⁽²⁷⁾,24-triene

tetraethylene glycol di(p-toluenesulfonate)

5-bromo-1,3-bis(bromomethyl)-2-methoxybenzene

(S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol

Downstream raw materials:

C₃₉H₄₁N₃O₁₅

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