(3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

Base Information

• Chemical Name: (3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol
• CAS No.: 1101107-81-6
• Molecular Formula: C₁₃H₁₇FO₄
• Molecular Weight: 256.274
• Mol file: 1101107-81-6.mol

Synonyms:(3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

Chemical Property of (3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol

There total 1 articles about (3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol 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: 24.0%

(2R,3R,4R)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran-3,4-diol (1009818-08-9) → (3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol (1101107-81-6)

Guidance literature:

With pyridine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 20 ℃; for 16h;

Reference yield: 52.0%

(3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol (1101107-81-6) + acetone (67-64-1) → 5-O-benzyl-3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-ribofuranose (1101107-84-9)

Guidance literature:

With hydrogenchloride; at 20 ℃; for 42h;

Reference yield:

(3S,4S,5R)-5-((benzyloxy)methyl)-4-fluoro-2-methoxytetrahydrofuran-3-ol (1101107-81-6) → ((2R,3R,4S)-5-acetoxy-4-(benzoyloxy)-3-fluorotetrahydrofuran-2-yl)methyl benzoate (123484-12-8)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 20 °C

2: pyridine / dichloromethane / 3 h / 0 - 20 °C

3: sulfuric acid; acetic anhydride; acetic acid / 16 h / 20 °C

With pyridine; sulfuric acid; palladium 10% on activated carbon; hydrogen; acetic anhydride; acetic acid; In ethanol; dichloromethane;

upstream raw materials:

(2R,3R,4R)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran-3,4-diol

Downstream raw materials:

5-O-benzyl-3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-ribofuranose

((2R,3R,4S)-5-acetoxy-4-(benzoyloxy)-3-fluorotetrahydrofuran-2-yl)methyl benzoate

N-(9-((2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide

N-(9-((2R,3S,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-fluoro-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide