2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

Base Information

Chemical Name:2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose
CAS No.:765311-75-9
Molecular Formula:C₁₆H₁₃FO₅
Molecular Weight:304.275
Hs Code.:

Synonyms:2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

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Chemical Property of 2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

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Technology Process of 2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

There total 5 articles about 2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose 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: 84.8%

: 765311-73-7
Benzoic acid (E)-(R)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

: 108-24-7
acetic anhydride

: 765311-75-9
2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1021/jo049597h

Reference yield:

: 765311-71-5
(2R,5R)-1-O-benzoyl-5,6-dihydroxy-3E-fluoro-2-hydroxy-2-ethynyl-3-hexene

: 765311-75-9
2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

Guidance literature:: Multi-step reaction with 2 steps

1: 91.9 percent / sodium periodate / ethanol; H₂O / 0.5 h / 20 °C

2: 84.8 percent / pyridine / 3 h / 20 °C

With pyridine; sodium periodate; In ethanol; water;
DOI:10.1021/jo049597h

Reference yield:

: 765311-67-9
(5R)-1-O-benzoyl-2-hydroxy-5,6-di(tert-butyldimethylsilyloxy)-3E-fluoro-3-hexene

: 765311-75-9
2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 4 h / 20 °C

2: 43.2 percent / tetrahydrofuran / 2 h / 50 °C

3: 97.5 percent / tetrabutylammonium fluoride; HOAc / tetrahydrofuran / 2 h / 20 °C

4: 91.9 percent / sodium periodate / ethanol; H₂O / 0.5 h / 20 °C

5: 84.8 percent / pyridine / 3 h / 20 °C

With pyridine; sodium periodate; tetrabutyl ammonium fluoride; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo049597h