2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester

Base Information

• Chemical Name: 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester
• CAS No.: 863660-52-0
• Molecular Formula: C₄₆H₆₈O₈Si
• Molecular Weight: 777.127

Synonyms:2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester

Chemical Property of 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester

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Technology Process of 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester

There total 21 articles about 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl 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:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester (863660-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / pyridine / 12 h / 0 °C

2.1: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran / 24 h / 60 °C

2.2: 70 percent / NaOH; H₂O₂ / tetrahydrofuran

3.1: 99 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C

4.1: 98 percent / triethylamine; sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 5 h / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: 61 percent / tetrahydrofuran / 6.5 h / -78 - 20 °C

6.1: 78 percent / NaHMDS / tetrahydrofuran / 0 - 20 °C

With pyridine; potassium phosphate; n-butyllithium; sulfur trioxide; hydrogen; sodium hexamethyldisilazane; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 2.1: Suzuki reaction / 5.2: Wittig reaction;

DOI:10.1021/jo0507993

Reference yield:

2,6-Dihydroxybenzoic acid (303-07-1) → 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester (863660-52-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / DMAP; SOCl₂ / 1,2-dimethoxy-ethane / 2 h / Heating

2.1: 90 percent / pyridine / 12 h / 0 °C

3.1: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran / 24 h / 60 °C

3.2: 70 percent / NaOH; H₂O₂ / tetrahydrofuran

4.1: 99 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C

5.1: 98 percent / triethylamine; sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 5 h / 0 - 20 °C

6.1: n-BuLi / tetrahydrofuran / 1 h / 0 - 20 °C

6.2: 61 percent / tetrahydrofuran / 6.5 h / -78 - 20 °C

7.1: 78 percent / NaHMDS / tetrahydrofuran / 0 - 20 °C

With pyridine; dmap; potassium phosphate; n-butyllithium; thionyl chloride; sulfur trioxide; hydrogen; sodium hexamethyldisilazane; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; dimethyl sulfoxide; 3.1: Suzuki reaction / 6.2: Wittig reaction;

DOI:10.1021/jo0507993

Reference yield:

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one (164014-40-8) → 2-Hydroxy-6-[3-((2S,6S)-6-vinyl-tetrahydro-pyran-2-yl)-propyl]-benzoic acid (1R,2S)-1-((S)-2-benzyloxy-3-{(2S,6R)-6-[1-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-tetrahydro-pyran-2-yl}-propyl)-2-methyl-but-3-enyl ester (863660-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran / 24 h / 60 °C

1.2: 70 percent / NaOH; H₂O₂ / tetrahydrofuran

2.1: 99 percent / hydrogen / Pd/C / methanol / 6 h / 20 °C

3.1: 98 percent / triethylamine; sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 5 h / 0 - 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / 0 - 20 °C

4.2: 61 percent / tetrahydrofuran / 6.5 h / -78 - 20 °C

5.1: 78 percent / NaHMDS / tetrahydrofuran / 0 - 20 °C

With pyridine; potassium phosphate; n-butyllithium; sulfur trioxide; hydrogen; sodium hexamethyldisilazane; triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 1.1: Suzuki reaction / 4.2: Wittig reaction;

DOI:10.1021/jo0507993

upstream raw materials:

2-Methyl-2-[(2R,6S)-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-propionic acid methyl ester

methyl 2-[(2R,6S)-tetrahydro-6-(2-hydroxyethyl)-2H-pyran-2-yl]-2-methylpropanoate

2-((2R,6S)-6-Carboxymethyl-tetrahydro-pyran-2-yl)-2-methyl-propionic acid methyl ester

2-[(2R,6S)-6-((R)-2-Hydroxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid methyl ester

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