(2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran

Base Information

• Chemical Name: (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran
• CAS No.: 107136-46-9
• Molecular Formula: C₁₉H₂₄O₆
• Molecular Weight: 348.396

Synonyms:

Chemical Property of (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran

There total 10 articles about (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran 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: 43.0%

sodium benzoate (532-32-1) + (2R,3R,4R,5S)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-bis<(methylsulfonyl)oxy>ethyl>-4-methyl-4-vinyltetrahydrofuran (103516-27-4) → (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran (107136-46-9) + (2R,3R,4R,5S)-5-<(1S)-1,2-bis(benzoyloxy)ethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran (103516-28-5)

Guidance literature:

In N,N-dimethyl-formamide; for 5h; Heating;

DOI:10.1021/jo00383a005

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (350255-13-9) → (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran (107136-46-9)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridinium chlorochromate (PCC), molecular sieves (4A, powder) / CH₂Cl₂

2: benzene / Heating

3: 92 percent / DIBAL-H / CH₂Cl₂ / 3 h / -30 °C

4: propanoic acid / 7 h / 135 °C

5: DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

6: pyridinium chlorochromate, molecular sieves (4A, powder) / CH₂Cl₂

7: 76 percent / 10percent palladium on charcoal / benzonitrile / 0.5 h / Heating

8: 93 percent / 50percent aq. CH₃COOH / 15 h / Ambient temperature

9: 90 percent / pyridine / 1 h / Ambient temperature

10: 11 percent / dimethylformamide / 5 h / Heating

With pyridine; palladium on activated charcoal; 4 A molecular sieve; diisobutylaluminium hydride; acetic acid; propionic acid; pyridinium chlorochromate; In dichloromethane; benzonitrile; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00383a005

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-ribo-3-hexulofuranose (2847-00-9) → (2R,3R,4R,5S)-5-<(1S)-2-(benzoyloxy)-1-hydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran (107136-46-9)

Guidance literature:

Multi-step reaction with 9 steps

1: benzene / Heating

2: 92 percent / DIBAL-H / CH₂Cl₂ / 3 h / -30 °C

3: propanoic acid / 7 h / 135 °C

4: DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 °C

5: pyridinium chlorochromate, molecular sieves (4A, powder) / CH₂Cl₂

6: 76 percent / 10percent palladium on charcoal / benzonitrile / 0.5 h / Heating

7: 93 percent / 50percent aq. CH₃COOH / 15 h / Ambient temperature

8: 90 percent / pyridine / 1 h / Ambient temperature

9: 11 percent / dimethylformamide / 5 h / Heating

With pyridine; palladium on activated charcoal; 4 A molecular sieve; diisobutylaluminium hydride; acetic acid; propionic acid; pyridinium chlorochromate; In dichloromethane; benzonitrile; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00383a005

upstream raw materials:

sodium benzoate

(2R,3R,4R,5S)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-bis<(methylsulfonyl)oxy>ethyl>-4-methyl-4-vinyltetrahydrofuran

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose

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