(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

Base Information

• Chemical Name: (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
• CAS No.: 852925-51-0
• Molecular Formula: C₂₃H₃₈O₆SSi
• Molecular Weight: 470.703
• Mol file: 852925-51-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 92.0%

(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) → (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 (852925-51-0)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2.5h;

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) → (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 (852925-51-0)

Guidance literature:

Multi-step reaction with 4 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

4: 92 percent / K₂CO₃ / methanol / 2.5 h / 20 °C

With 1H-imidazole; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; 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 → (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 (852925-51-0)

Guidance literature:

Multi-step reaction with 5 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

5: 92 percent / K₂CO₃ / methanol / 2.5 h / 20 °C

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

DOI:10.1021/ol050477l

upstream raw materials:

(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

(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

(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