(-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran

Base Information

• Chemical Name: (-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran
• CAS No.: 875545-11-2
• Molecular Formula: C₂₅H₄₀O₇Si
• Molecular Weight: 480.674
• Mol file: 875545-11-2.mol

Synonyms:(-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran

Chemical Property of (-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran

There total 1 articles about (-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran 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: 76.0%

[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol (875545-10-1) + acetic anhydride (108-24-7) → (-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran (875545-11-2)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2005.08.112

Reference yield:

(-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran (875545-11-2) → (+)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-benzoyloxy-tetrahydropyran-4-one (875545-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

2.1: molecular sieves 4 Angstroem; N-methylmorpholine N-oxide / CH₂Cl₂ / 0.17 h / 20 °C

2.2: 82 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂

3.1: anhydrous FeCl₃ / CH₂Cl₂ / 0 - 20 °C

3.2: 56 percent / CH₂Cl₂ / 0.17 h

With 4 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.08.112

Reference yield:

(-)-(2R,3S,4R,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-4-(tert-butyldimethylsilanyloxy)-tetrahydropyran (875545-11-2) → (2R,3R,6R)-2,6-bis-acetoxymethyl-3-benzoyloxy-tetrahydropyran-4-one

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

2.1: molecular sieves 4 Angstroem; N-methylmorpholine N-oxide / CH₂Cl₂ / 0.17 h / 20 °C

2.2: 82 percent / tetra-n-propylammonium perruthenate / CH₂Cl₂

3.1: anhydrous FeCl₃ / CH₂Cl₂ / 0 - 20 °C

3.2: 56 percent / CH₂Cl₂ / 0.17 h

4.1: triethylamine / Heating

With 4 A molecular sieve; tetrabutyl ammonium fluoride; iron(III) chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2005.08.112

upstream raw materials:

[(2R,3S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxymethyl-3-((S)-1-phenyl-ethoxy)-tetrahydro-pyran-2-yl]-methanol

acetic anhydride

Downstream raw materials:

(+)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-benzoyloxy-tetrahydropyran-4-one

(-)-(2R,3S,6R)-2,6-bis-acetoxymethyl-3-((S)-1-phenylethoxy)-tetrahydropyran-4-one