(R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one

Base Information

• Chemical Name: (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one
• CAS No.: 633305-50-7
• Molecular Formula: C₁₉H₂₁NO₆
• Molecular Weight: 359.379
• Mol file: 633305-50-7.mol

Synonyms:(R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one

Chemical Property of (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one

There total 1 articles about (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one 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: 90.0%

5-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-1-hydroxy-7-(4-methoxy-benzyloxy)-hept-1-en-3-one (633305-47-2) → (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one (633305-50-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1055/s-2003-41462

Reference yield: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one (633305-50-7) → 6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one (633305-51-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1055/s-2003-41462

Reference yield:

(R)-6-(2-Hydroxymethyl-oxazol-4-yl)-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one (633305-50-7) → 1-{4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-tetrahydro-pyran-2-yl}-8-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-6-(4-methoxy-benzyloxy)-octan-4-one

Guidance literature:

Multi-step reaction with 7 steps

1.1: 97 percent / imidazole / dimethylformamide / 5 h / 20 °C

2.1: 95 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.33 h / -78 °C

3.1: 95 percent / H₂ / Pd/C / ethyl acetate / 8 h / 20 °C

4.1: imidazole; DMAP / dimethylformamide / 20 °C

5.1: DDQ / CH₂Cl₂ / 2 h / 20 °C / pH 7

6.1: 326 mg / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: TiCl₄ / tetrahydrofuran / 0.5 h / -78 °C

7.2: 334 mg / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; cerium(III) chloride; hydrogen; titanium tetrachloride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: Luche reduction / 6.1: Dess-Martin oxidation;

DOI:10.1002/chem.200500892

upstream raw materials:

5-(tert-butyl-dimethyl-silanyloxy)-1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-1-hydroxy-7-(4-methoxy-benzyloxy)-hept-1-en-3-one

Downstream raw materials:

6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-2,3-dihydro-pyran-4-one

6-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-2-[2-(4-methoxy-benzyloxy)-ethyl]-3,4-dihydro-2H-pyran-4-ol

(2R,4S,6R)-2-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-4-ol

4-{4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole