(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

Base Information

Chemical Name:(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide
CAS No.:1402931-83-2
Molecular Formula:C₃₃H₃₇NO₁₀
Molecular Weight:607.657
Hs Code.:

(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

Synonyms:(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

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Chemical Property of (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

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Technology Process of (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

There total 18 articles about (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide 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:

: 960365-65-5
(1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate

: 1402931-83-2
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine / toluene / 0.17 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere; Molecular sieve

2.1: lithium hydroxide / methanol; water / 16 h / 45 °C / Inert atmosphere

2.2: pH 5 - 6 / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.2: 12.16 h / 0 - 20 °C / Inert atmosphere

4.1: 10% palladium hydroxide on charcoal; hydrogen / tetrahydrofuran / 760.05 Torr / Inert atmosphere

With 10% palladium hydroxide on charcoal; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/jm3011542

Reference yield:

: C₄₀H₄₃NO₁₀

: 1402931-83-2
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

Guidance literature:: With 10% palladium hydroxide on charcoal; hydrogen; In tetrahydrofuran; under 760.051 Torr; Inert atmosphere;
DOI:10.1021/jm3011542

Reference yield:

: [2-[4-benzyloxy-2-methoxy-6-(4-methoxybenzoyl)oxyphenyl]-2-oxoethyl] 4-methoxybenzoate

: 1402931-83-2
(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6-((2S,6S)-6-(hydroxymethyl)-1,4-dioxan-2-yloxy)-8-methoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]-furan-2-carboxamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 - -20 °C / Inert atmosphere

2.1: sulfuric acid; acetic acid / 20 h / 20 °C / Inert atmosphere

3.1: water; sodium hydroxide / ethanol / 1 h / 80 °C / Inert atmosphere

4.1: methanol; dichloromethane; acetonitrile / 10 h / 0 - 5 °C / Inert atmosphere; UV-irradiation

4.2: 1 h / 60 °C / Inert atmosphere

4.3: 48 h / Inert atmosphere

5.1: 5%-palladium/activated carbon; hydrogen / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

6.1: ChiralPak AD-H / ethanol / Inert atmosphere; Supercritical conditions; Resolution of racemate

7.1: triphenylphosphine / toluene / 0.17 h / 0 °C / Inert atmosphere

7.2: 2 h / 0 °C / Inert atmosphere; Molecular sieve

8.1: lithium hydroxide / methanol; water / 16 h / 45 °C / Inert atmosphere

8.2: pH 5 - 6 / Inert atmosphere

9.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

9.2: 12.16 h / 0 - 20 °C / Inert atmosphere

10.1: 10% palladium hydroxide on charcoal; hydrogen / tetrahydrofuran / 760.05 Torr / Inert atmosphere

With sulfuric acid; 10% palladium hydroxide on charcoal; 5%-palladium/activated carbon; water; hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; sodium hydroxide; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile; 1.1: |Baker-Venkataraman Rearrangement;
DOI:10.1021/jm3011542