3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

Base Information

• Chemical Name: 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate
• CAS No.: 529488-11-7
• Molecular Formula: C₃₂H₃₈O₆Si
• Molecular Weight: 546.736
• Mol file: 529488-11-7.mol

Synonyms:3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

Chemical Property of 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate

There total 3 articles about 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl 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: 68.0%

{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane (529488-06-0) → 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate (529488-11-7)

Guidance literature:

{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane; With oxygen; ozone; In dichloromethane; at -78 ℃; for 0.5h;

With oxygen; triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 4h; Further stages.;

DOI:10.1039/b209637b

Reference yield:

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate (529488-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / pyridine / CH₂Cl₂ / 0.25 h / -12 °C

2.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

2.2: 59 percent / CuBr / tetrahydrofuran / 14 h / 0 °C

3.1: O₃/O₂ / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 68 percent / PPh₃; O₂ / CH₂Cl₂ / 4 h / -78 - 20 °C

With pyridine; iodine; oxygen; ozone; magnesium; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b209637b

Reference yield:

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (529488-04-8) → 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate (529488-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg; I₂ / tetrahydrofuran / 1 h / 20 °C

1.2: 59 percent / CuBr / tetrahydrofuran / 14 h / 0 °C

2.1: O₃/O₂ / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 68 percent / PPh₃; O₂ / CH₂Cl₂ / 4 h / -78 - 20 °C

With iodine; oxygen; ozone; magnesium; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b209637b

upstream raw materials:

{(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside

Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid