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

Base Information

• Chemical Name: (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole
• CAS No.: 265666-22-6
• Molecular Formula: C₂₉H₄₅NO₆Si
• Molecular Weight: 531.765
• Mol file: 265666-22-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole 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%

(2'R,4'R,6'R)-3''-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-propane-1'',2''-diol (265666-21-5) → (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole (265666-22-6)

Guidance literature:

With sodium hydride; N-tosylimidazole;

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

Reference yield:

(4S,1'R)-4-(1'-hydroxybut-3'-enyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (132328-52-0) → (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole (265666-22-6)

Guidance literature:

Multi-step reaction with 16 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

14.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

14.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

15.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

16.1: NaH / tetrahydrofuran / 1 h / 20 °C

16.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol; 6.1: Wittig reaction / 8.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

Reference yield:

(4S,1'R)-2,2-dimethyl-4-[3'-oxo-1'-(triethylsilanyloxy)-propyl]-oxazolidine-3-carboxylic acid tert-butyl ester (265666-15-7) → (2'R,4'R,6'R)-2-(4-methoxybenzyloxymethyl)-4-(6'-oxiranylmethyl-4'-triisopropylsilanyloxy-tetrahydropyran-2'-yl)-oxazole (265666-22-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diethyl ether / 2.25 h / -78 °C

1.2: 76 percent / Et₃N; aq. H₂O₂ / diethyl ether / 12 h / 20 °C

2.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 1.25 h / -78 °C

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

3.2: 95 percent / PPh₃ / CH₂Cl₂ / 14 h / 20 °C

4.1: 87 percent / CH₂Cl₂ / 14 h / 20 °C

5.1: 84 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

6.1: 87 percent / NaHMDS / tetrahydrofuran / 1 h / -78 °C

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

8.1: 1.34 g / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / tetrahydrofuran / 20 h / 20 °C

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

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

10.2: 0.65 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; acetonitrile / 1 h / 20 °C

11.1: 87 percent / DIBALH / toluene / 2.5 h / -78 °C

12.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 0 °C

12.2: 59 percent / hexane; tetrahydrofuran / 16 h / -78 - 20 °C

13.1: 50 percent / (DHQD)2PYR; K₂OsO₂(OH)4; K₃Fe(CN)6 / aq. K₂CO₃ / 2-methyl-propan-2-ol

14.1: NaH / tetrahydrofuran / 1 h / 20 °C

14.2: 76 percent / N-tosylimidazole / tetrahydrofuran / 3 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-pyridine; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium dioxotetrahydroxoosmate(VI); dibromotetrachloroethane; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; Dess-Martin periodane; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; toluene; tert-butyl alcohol; 4.1: Wittig reaction / 6.1: oxy-anion intramolecular Michael reaction;

DOI:10.1039/b308305e

upstream raw materials:

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

p-methoxybenzyloxy acetic acid

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

(4S,1'R)-2,2-dimethyl-4-[3'-oxo-1'-(triethylsilanyloxy)-propyl]-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(2'R,4'R,6'R,4''R)-4-(2'',2''-dimethyl-[1'',3'']-dioxan-4''-ylmethyl)-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl}-pent-4-en-2-ol

(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

(2'S,4'R,6'R,5R)-methanesulfonic acid 5,7-dihydroxy-1-{6'-[2-(4-methoxybenzyloxymethyl)-oxazol-4-yl]-4'-(triisopropylsilanyloxy)-tetrahydropyran-2'-yl-methyl}-3-methyleneheptyl ester

Methanesulfonic acid 3-((R)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-1-{(2S,4R,6R)-6-[2-(4-methoxy-benzyloxymethyl)-oxazol-4-yl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-ylmethyl}-but-3-enyl ester