3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester

Base Information

• Chemical Name: 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester
• CAS No.: 197716-43-1
• Molecular Formula: C₃₆H₄₆O₈
• Molecular Weight: 606.756
• Mol file: 197716-43-1.mol

Synonyms:3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester

Chemical Property of 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester

There total 13 articles about 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl 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: 92.0%

3-oxooctanoic acid (13283-91-5) + (2S,3R,4R)-2,3,5-Tris-benzyloxy-4-methoxymethoxy-pentan-1-ol → 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester (197716-43-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.3987/COM-97-7926

Reference yield:

ethyl β-hydroxyoctanoate (7367-90-0,96854-38-5,112138-04-2,118918-31-3) → 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester (197716-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Jones oxidation

2: KOH

3: 92 percent / DCC, DMAP / CH₂Cl₂

With dmap; potassium hydroxide; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.3987/COM-97-7926

Reference yield:

benzyl bromide (100-39-0) → 3-Oxo-octanoic acid (2S,3R,4R)-2,3,5-tris-benzyloxy-4-methoxymethoxy-pentyl ester (197716-43-1)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.3987/COM-97-7926

upstream raw materials:

3-oxooctanoic acid

ethyl β-hydroxyoctanoate

benzyl bromide

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

Downstream raw materials:

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

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