4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 210427-09-1
• Molecular Formula: C₃₁H₃₈O₁₁
• Molecular Weight: 586.636
• Mol file: 210427-09-1.mol

Synonyms:4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl 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: 64.0%

levulinic acid (123-76-2) + (2S,3R,4S,5R,6R)-2-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (186504-17-6) → 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (210427-09-1)

Guidance literature:

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In 1,4-dioxane; at 20 ℃; for 42h;

DOI:10.1021/ja0022730

Reference yield:

(3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one (163129-59-7) → 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (210427-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe; MeOH / tetrahydrofuran / 4.5 h

2: 64 percent / 2-chloro-1-methylpyridinium iodide; Et₃N / dioxane / 42 h / 20 °C

With methanol; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; triethylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/ja0022730

Reference yield:

(3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one (163228-32-8) → 4-Oxo-pentanoic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4R)-4-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (210427-09-1)

Guidance literature:

Multi-step reaction with 3 steps

1: TBAF / tetrahydrofuran / 18 h

2: NaOMe; MeOH / tetrahydrofuran / 4.5 h

3: 64 percent / 2-chloro-1-methylpyridinium iodide; Et₃N / dioxane / 42 h / 20 °C

With methanol; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; sodium methylate; triethylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/ja0022730

upstream raw materials:

levulinic acid

(2S,3R,4S,5R,6R)-2-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

(3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-hydroxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

(3aS,4R,6S,7R,7aR)-6-((2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-7-hydroxy-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one