(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

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Chemical Name:(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one
CAS No.:499121-02-7
Molecular Formula:C₃₇H₆₄O₁₀Si₂
Molecular Weight:725.08
Hs Code.:

Synonyms:(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

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Chemical Property of (3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

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Technology Process of (3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

There total 22 articles about (3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one 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:

: 499121-01-6
(2R,3S,4R)-4-benzyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide

: 499121-02-7
(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / pyridine / 12 h / 50 °C

2.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

3.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

4.2: tetrahydrofuran; toluene / 1 h / -78 °C

With pyridine; hydrogen; potassium hexamethylsilazane; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; 3.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 499121-00-5
(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

: 499121-02-7
(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1.11 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 72 h / 20 °C

2.1: 95 percent / pyridine / 12 h / 50 °C

3.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

4.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

5.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

5.2: tetrahydrofuran; toluene / 1 h / -78 °C

With pyridine; N-iodo-succinimide; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; 4.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 499121-08-3
(2R,3S,4R)-4-benzyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-bis(triethylsiloxy)-4-butanolide

: 499121-02-7
(3S,4S,5R)-5-Benzyl-3-((Z)-(4R,5S)-3-hydroxy-4,5-bis-methoxymethoxy-2-methyl-non-6-enoyl)-3,4-bis-triethylsilanyloxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / H₂ / Pd/C / ethanol / 72 h

2.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 9 h / 20 °C

3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: tetrahydrofuran; toluene / 1 h / -78 °C

With hydrogen; potassium hexamethylsilazane; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene; 2.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703