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

Base Information

• Chemical Name: 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid
• CAS No.: 529488-16-2
• Molecular Formula: C₃₂H₃₈O₇Si
• Molecular Weight: 562.735
• Mol file: 529488-16-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid 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: 94.0%

3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate (529488-11-7) → 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid (529488-16-2)

Guidance literature:

With sodium chlorite; dihydrogen peroxide; sodium hydrogensulfite; sodium dihydrogenphosphate; In acetonitrile; at 20 ℃; for 3.5h;

DOI:10.1039/b209637b

Reference yield:

methyl 3-O-[tert-butyl-(diphenyl)silyl]-2,4-dideoxy-D-threo-hexopyranoside (530112-01-7) → 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid (529488-16-2)

Guidance literature:

Multi-step reaction with 4 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

4.1: 94 percent / NaClO₂; NaHSO₃; aq. H₂O₂ / NaH₂PO₄ / acetonitrile / 3.5 h / 20 °C

With pyridine; sodium chlorite; dihydrogen peroxide; iodine; oxygen; ozone; sodium hydrogensulfite; magnesium; sodium dihydrogenphosphate; In tetrahydrofuran; dichloromethane; acetonitrile;

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) → 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid (529488-16-2)

Guidance literature:

Multi-step reaction with 3 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

3.1: 94 percent / NaClO₂; NaHSO₃; aq. H₂O₂ / NaH₂PO₄ / acetonitrile / 3.5 h / 20 °C

With sodium chlorite; dihydrogen peroxide; iodine; oxygen; ozone; sodium hydrogensulfite; magnesium; sodium dihydrogenphosphate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1039/b209637b

upstream raw materials:

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

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

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