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

Base Information

• Chemical Name: 3-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-one
• CAS No.: 197716-46-4
• Molecular Formula: C₂₂H₂₈O₇
• Molecular Weight: 404.46
• Mol file: 197716-46-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 3-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-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:

2,3,5-tri-O-benzyl-D-xylitol (100896-16-0) → 3-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-one (197716-46-4)

Guidance literature:

Multi-step reaction with 7 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

7: 1.) PCC, MS₄A; 2.) SiO₂ / 1.) CH₂Cl₂; 2.) hexane, EtOAc

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; silica gel; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; 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-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-one (197716-46-4)

Guidance literature:

Multi-step reaction with 9 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

9: 1.) PCC, MS₄A; 2.) SiO₂ / 1.) CH₂Cl₂; 2.) hexane, EtOAc

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

DOI:10.3987/COM-97-7926

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 3-Hexanoyl-4-((4R,5R)-5-methoxymethoxy-2-phenyl-[1,3]dioxan-4-yl)-5H-furan-2-one (197716-46-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / NaH / tetrahydrofuran

2: 93 percent / conc. HCl

3: 98 percent / NaH / tetrahydrofuran

4: 91 percent / 80percent CH₃COOH / 100 °C

5: 96 percent / NaBH₄ / ethanol

6: 92 percent / imidazole / dimethylformamide

7: 97 percent / diisopropylethylamine / CH₂Cl₂

8: 98 percent / Bu₄NF / tetrahydrofuran

9: 92 percent / DCC, DMAP / CH₂Cl₂

10: 94 percent / Pd (black) / formic acid; methanol / 40 °C

11: 60 percent / p-TsOH

12: 1.) PCC, MS₄A; 2.) SiO₂ / 1.) CH₂Cl₂; 2.) hexane, EtOAc

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

DOI:10.3987/COM-97-7926

upstream raw materials:

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

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