2H-Pyran-2-acetaldehyde, tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1 -methylethyl)silyl]oxy]-, (2S,4R,6R)-

Base Information

• Chemical Name: 2H-Pyran-2-acetaldehyde, tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1 -methylethyl)silyl]oxy]-, (2S,4R,6R)-
• CAS No.: 265666-31-7
• Molecular Formula: C28H43NO6Si
• Molecular Weight: 517.738
• Mol file: 265666-31-7.mol

Synonyms:

Chemical Property of 2H-Pyran-2-acetaldehyde, tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1 -methylethyl)silyl]oxy]-, (2S,4R,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-acetaldehyde, tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1 -methylethyl)silyl]oxy]-, (2S,4R,6R)-

There total 22 articles about 2H-Pyran-2-acetaldehyde, tetrahydro-6-[2-[[(4-methoxyphenyl)methoxy]methyl]-4-oxazolyl]-4-[[tris(1 -methylethyl)silyl]oxy]-, (2S,4R,6R)- 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: 87.0%

(2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetic acid ethyl ester (265666-19-1) → (2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetaldehyde (265666-31-7)

Guidance literature:

With diisobutylaluminium hydride;

DOI:10.1016/S0040-4039(99)02187-5

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetaldehyde (265666-31-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

3.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

4.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

5.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

6.1: aq. HCl / dioxane / 1.33 h / 20 °C

7.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

9.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

10.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; 2,6-di-tert-butyl-pyridine; dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene; 3.1: Wittig reaction / 5.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

Reference yield:

(4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (132328-52-0) → (2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetaldehyde (265666-31-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 90 percent / DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2.1: O₃; NaHCO₃ / CH₂Cl₂ / 1 h / -78 °C

2.2: 92 percent / PPh₃ / CH₂Cl₂ / 14 h / -78 - 20 °C

3.1: diethyl ether / 2.25 h / -78 °C

3.2: 76 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

4.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

5.1: ozone; NaHCO₃ / CH₂Cl₂ / 0.5 h / -78 °C

5.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

6.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

7.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

8.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

9.1: aq. HCl / dioxane / 1.33 h / 20 °C

10.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

12.1: PPh₃; 2,6-di-tert-butylpyridine; dibromotetrachloroethane / CH₂Cl₂ / 3 h / 20 °C

12.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

13.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; 2,6-di-tert-butyl-pyridine; dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; toluene; 6.1: Wittig reaction / 8.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

upstream raw materials:

(2'S,4'R,6'R)-[6'-{2-(4-methoxybenzyloxymethyl)-oxazol-4-yl}-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl]-acetic acid ethyl ester

p-methoxybenzyloxy acetic acid

triisopropylsilyl trifluoromethanesulfonate

(4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(2'R,4'R,6'R)-4-(6'-allyl-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl)-2-(4-methoxybenzyloxymethyl)-oxazole

(2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole

(2'R,4'R,6'R)-3''-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-propane-1'',2''-diol

(2'R,4'R,6'R,2R,6R)-2''-({6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-4-methylene-tetrahydropyran-2-yl)-ethanol