1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

Base Information

Chemical Name:1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose
CAS No.:634181-84-3
Molecular Formula:C₂₁H₂₀F₂O₆
Molecular Weight:406.383
Hs Code.:

Synonyms:1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

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Chemical Property of 1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

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Technology Process of 1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

There total 11 articles about 1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose 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: 94.0%

: 108-24-7
acetic anhydride

: ((2R,4R)-4-(benzyloxy)-3,3-difluoro-5-hydroxytetrahydrofuran-2-yl)methyl benzoate

: 1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-β-D-arabinofuranose

: 634181-84-3
1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

Guidance literature:: With dmap; In dichloromethane; at 20 ℃;
DOI:10.1021/jo034512i

Reference yield:

: 98-88-4
benzoyl chloride

: 634181-84-3
1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 2 h / -70 °C

2: aq. AcOH / 1.5 h / 50 °C

3: aq. NaIO₄ / 1.5 h / 20 °C

4: 94 percent / DMAP / CH₂Cl₂ / 20 °C

With pyridine; dmap; sodium periodate; acetic acid; In dichloromethane;
DOI:10.1021/jo034512i

Reference yield:

: 100-39-0
benzyl bromide

: 634181-84-3
1-O-acetyl-2-O-benzyl-5-O-benzoyl-3-deoxy-3,3-difluoro-α-D-arabinofuranose

Guidance literature:: Multi-step reaction with 6 steps

1: NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

2: 47.5 percent / OsO₄; NMNO; H₂O / acetone / 48 h / 20 °C

3: 90 percent / pyridine / CH₂Cl₂ / 2 h / -70 °C

4: aq. AcOH / 1.5 h / 50 °C

5: 4.328 g / aq. NaIO₄ / 1.5 h / 20 °C

6: 94 percent / DMAP / CH₂Cl₂ / 20 °C

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; water; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/jo034512i