(2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran

Base Information

• Chemical Name: (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran
• CAS No.: 154738-23-5
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 154738-23-5.mol

Synonyms:(2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran

Chemical Property of (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran

There total 5 articles about (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran 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:

(2S,3R,5R)-3-<(benzoyloxy)methyl>-2-<2-<(tert-butyl)diphenylsilyloxy>ethyl>-5-methoxytetrahydrofuran → (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran (154738-23-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 5h; Yield given;

DOI:10.1002/hlca.19930760821

Reference yield:

dimethyl (2S,3S)-2-allyl-3-hydroxyglutarate (147528-53-8) → (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran (154738-23-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) O₃, 2.) Me₂S, 3.) Dowex 50W X₈-H(+) / 1.) -78 deg C, 2 h, 2.) 12 h, 3.) reflux , 5 h

2: 94 percent / LiAlH₄ / diethyl ether / Ambient temperature

3: 450 mg / imidazole / CH₂Cl₂ / Ambient temperature

4: pyridine / 0.5 h / Ambient temperature

5: Bu₄NF*3H₂O / tetrahydrofuran / 5 h

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; dimethylsulfide; Dowex 50W X₈-H(+); tetrabutyl ammonium fluoride; ozone; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/hlca.19930760821

Reference yield:

(2S,3R,5R)-2-(hydroxyethyl)-3-(hydroxymethyl)-5-methoxytetrahydrofuran (154738-17-7) → (2S,3R,5R)-3-<(benzoyloxy)methyl>-2-(2-hydroxyethyl)-5-methoxytetrahydrofuran (154738-23-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 450 mg / imidazole / CH₂Cl₂ / Ambient temperature

2: pyridine / 0.5 h / Ambient temperature

3: Bu₄NF*3H₂O / tetrahydrofuran / 5 h

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/hlca.19930760821

upstream raw materials:

dimethyl (2S,3S)-2-allyl-3-hydroxyglutarate

(2S,3R,5R)-2-(hydroxyethyl)-3-(hydroxymethyl)-5-methoxytetrahydrofuran

(2S,3R,5R)-2-<2-<(tert-butyl)diphenylsilyloxy>ethyl>-3-(hydroxymethyl)-5-methoxytetrahydrofuran

(2S,3S,5R)-5-methoxy-3-(methoxycarbonyl)-2-<(methoxycarbonyl)methyl>tetrahydrofuran

Downstream raw materials:

(1S,5S,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo<3.2.1>octane