9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine

Base Information

• Chemical Name: 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine
• CAS No.: 765311-81-7
• Molecular Formula: C₂₃H₂₀FN₅O₄
• Molecular Weight: 449.441

Synonyms:9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine

Chemical Property of 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine

Chemical Property:

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Technology Process of 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine

There total 6 articles about 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N⁶-isobutyryladenine 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: 32.1%

2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose (765311-75-9) + N6-(2-methylpropionyl)adenine (109153-46-0) → 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-α-D-furanosyl)-N6-isobutyryladenine + 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N6-isobutyryladenine (765311-81-7)

Guidance literature:

N⁶-(2-methylpropionyl)adenine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 50 - 60 ℃; for 2h;

2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-5-O-benzoyl-1-O-acetyl-D-furanose; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1021/jo049597h

Reference yield:

Benzoic acid (E)-(R)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester (765311-73-7) → 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N6-isobutyryladenine (765311-81-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84.8 percent / pyridine / 3 h / 20 °C

2.1: N,O-bis(trimethylsiyl)acetamide / acetonitrile / 2 h / 50 - 60 °C

2.2: 32.1 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile;

DOI:10.1021/jo049597h

Reference yield:

(2R,5R)-1-O-benzoyl-5,6-dihydroxy-3E-fluoro-2-hydroxy-2-ethynyl-3-hexene (765311-71-5) → 9-(5-O-benzoyl-2,3-dideoxy-2,3-didehydro-3-fluoro-4-ethynyl-β-D-furanosyl)-N6-isobutyryladenine (765311-81-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91.9 percent / sodium periodate / ethanol; H₂O / 0.5 h / 20 °C

2.1: 84.8 percent / pyridine / 3 h / 20 °C

3.1: N,O-bis(trimethylsiyl)acetamide / acetonitrile / 2 h / 50 - 60 °C

3.2: 32.1 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 20 °C

With pyridine; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; In ethanol; water; acetonitrile;

DOI:10.1021/jo049597h

upstream raw materials:

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

N⁶-(2-methylpropionyl)adenine

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

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

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