(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

Base Information

• Chemical Name: (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
• CAS No.: 548485-22-9
• Molecular Formula: C₃₃H₄₁BrO₈
• Molecular Weight: 645.588

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 36.0%

tetraethylene glycol di(p-toluenesulfonate) (37860-51-8) + 5-bromo-1,3-bis[(4S)-4-hydroxy-4-phenyl-2-oxobutyl]-2-methoxybenzene (497107-20-7) → (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)

Guidance literature:

With sodium hydride;

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

Reference yield:

5-bromo-1,3-bis(bromomethyl)-2-methoxybenzene (118249-11-9) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 3 h / Heating

1.2: tetrahydrofuran / 6 h / Heating

2.1: 14.9 g / pyridinium p-toluenesulfonate / ethanol / 12 h / 50 °C

3.1: 36 percent / NaH / tetrahydrofuran / 60 °C

With pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; ethanol;

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

Reference yield:

(S)-(+)-2-phenyl-2-(tetrahydropyranyloxy)ethanol (94199-20-9) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 3 h / Heating

1.2: tetrahydrofuran / 6 h / Heating

2.1: 14.9 g / pyridinium p-toluenesulfonate / ethanol / 12 h / 50 °C

3.1: 36 percent / NaH / tetrahydrofuran / 60 °C

With pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; ethanol;

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

upstream raw materials:

tetraethylene glycol di(p-toluenesulfonate)

5-bromo-1,3-bis[(4S)-4-hydroxy-4-phenyl-2-oxobutyl]-2-methoxybenzene

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

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

Downstream raw materials:

(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

(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

C₃₉H₄₁BrN₂O₁₃

C₃₂H₃₉BrO₈

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