3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester

Base Information

• Chemical Name: 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester
• CAS No.: 197716-45-3
• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.491
• Mol file: 197716-45-3.mol

Synonyms:

Chemical Property of 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester

There total 11 articles about 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester 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: 60.0%

benzaldehyde dimethyl acetal (1125-88-8) + 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-trihydroxy-4-methoxymethoxy-pentyl ester → 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester (197716-45-3)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.3987/COM-97-7926

Reference yield:

2,3,5-tri-O-benzyl-D-xylitol (100896-16-0) → 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester (197716-45-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 92 percent / imidazole / dimethylformamide

2: 97 percent / diisopropylethylamine / CH₂Cl₂

3: 98 percent / Bu₄NF / tetrahydrofuran

4: 92 percent / DCC, DMAP / CH₂Cl₂

5: 94 percent / Pd (black) / formic acid; methanol / 40 °C

6: 60 percent / p-TsOH

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; methanol; formic acid; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-7926

Reference yield:

2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside (197716-38-4) → 3-Oxo-octanoic acid (S)-2-hydroxy-2-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl ester (197716-45-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / 80percent CH₃COOH / 100 °C

2: 96 percent / NaBH₄ / ethanol

3: 92 percent / imidazole / dimethylformamide

4: 97 percent / diisopropylethylamine / CH₂Cl₂

5: 98 percent / Bu₄NF / tetrahydrofuran

6: 92 percent / DCC, DMAP / CH₂Cl₂

7: 94 percent / Pd (black) / formic acid; methanol / 40 °C

8: 60 percent / p-TsOH

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; methanol; formic acid; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-7926

upstream raw materials:

benzaldehyde dimethyl acetal

3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose

2,3,5-tri-O-benzyl-D-xylitol

Downstream raw materials:

3-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-one