((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Base Information

• Chemical Name: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 125291-12-5
• Molecular Formula: C₁₅H₁₇FO₅
• Molecular Weight: 296.295
• Mol file: 125291-12-5.mol

Synonyms:((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property of ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

There total 17 articles about ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 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: 99.8%

3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranose (18530-84-2) + benzoyl chloride (98-88-4) → ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (125291-12-5)

Guidance literature:

With pyridine; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(94)84007-5

Reference yield: 82.0%

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (6612-91-5) → ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (125291-12-5)

Guidance literature:

With dmap; diethylamino-sulfur trifluoride; In dichloromethane;

DOI:10.1016/S0040-4039(00)99193-7

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (125291-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 11.37 g / NaBH₄ / tetrahydrofuran; H₂O / 0.25 h / 0 °C

2: 81 percent / diethylaminosulfur trifluoride; pyridine / CH₂Cl₂ / 96 h / 20 °C

With pyridine; sodium tetrahydroborate; diethylamino-sulfur trifluoride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bmc.2003.10.012

upstream raw materials:

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranose

benzoyl chloride

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

Downstream raw materials:

9-(2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine

9-(3-deoxy-3-fluoro-β-D-xylofuranosyl)guanine

N2-acetyl-9-(5-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine

1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-β-D-xylofuranosyl)thymine