(3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate

Base Information

• Chemical Name: (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate
• CAS No.: 852925-50-9
• Molecular Formula: C₂₇H₄₂O₈SSi
• Molecular Weight: 554.777
• Mol file: 852925-50-9.mol

Synonyms:(3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate

Chemical Property of (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate

There total 4 articles about (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate 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: 98.0%

(2R,3S,4R,6S)-3,6-di(acetyloxy)-2-[(4R,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydro-2H-4-pyranyl acetate (852925-49-6) + phenylthiotrimethylsilane (4551-15-9) → (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate (852925-50-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; zinc(II) iodide; In 1,2-dichloro-ethane; at 0 ℃; for 2h;

DOI:10.1021/ol050477l

Reference yield:

(2R,3S,4R,6S)-3,6-di(acetyloxy)-2-(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yltetrahydro-2H-4-pyranyl acetate (852925-47-4) → (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate (852925-50-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / H₂ / Pd/C / methanol / 24 h / 20 °C

2: 97 percent / imidazole / dimethylformamide / 14 h / 20 °C

3: 98 percent / n-tetrabutylammonium iodide; ZnI₂ / 1,2-dichloro-ethane / 2 h / 0 °C

With 1H-imidazole; hydrogen; tetra-(n-butyl)ammonium iodide; zinc(II) iodide; palladium on activated charcoal; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050477l

Reference yield:

(2R,6R)-6-((4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-4,5-dihydroxytetrahydro-2H-2-pyranyl acetate → (3S,4R,6S)-3-(acetyloxy)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-4-pyranyl acetate (852925-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine / 16 h / 20 °C

2: 94 percent / H₂ / Pd/C / methanol / 24 h / 20 °C

3: 97 percent / imidazole / dimethylformamide / 14 h / 20 °C

4: 98 percent / n-tetrabutylammonium iodide; ZnI₂ / 1,2-dichloro-ethane / 2 h / 0 °C

With pyridine; 1H-imidazole; hydrogen; tetra-(n-butyl)ammonium iodide; zinc(II) iodide; palladium on activated charcoal; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050477l

upstream raw materials:

(2R,3S,4R,6S)-3,6-di(acetyloxy)-2-[(4R,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]tetrahydro-2H-4-pyranyl acetate

phenylthiotrimethylsilane

(2R,3S,4R,6S)-3,6-di(acetyloxy)-2-(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yltetrahydro-2H-4-pyranyl acetate

(2R,3S,4R,6S)-3,6-di(acetyloxy)-2-(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yltetrahydro-2H-4-pyranyl acetate

Downstream raw materials:

(2R,3R,4R)-2-[(4S,5R)-5-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-(phenylsulfanyl)tetrahydro-2H-3,4-pyrandiol