1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose

Base Information

• Chemical Name: 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose
• CAS No.: 786709-74-8
• Molecular Formula: C₂₆H₂₅FO₅
• Molecular Weight: 436.48
• Mol file: 786709-74-8.mol

Synonyms:1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose

Chemical Property of 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose

There total 8 articles about 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose 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: 59.0%

1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-lyxitol (786709-72-6) → 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose (786709-74-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.166667h;

DOI:10.1021/ol048459b

Reference yield:

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (19139-80-1,34370-91-7,68354-70-1,70798-12-8,59358-33-7) → 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose (786709-74-8)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / 0.5 h

2: 1.36 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 °C

3: sulfuric acid / 2 h / Heating

4: 1.28 g / NaH / dimethylformamide / 20 °C

5: 88 percent / hydrochloric acid / dioxane / Heating

6: 92 percent / NaBH₄ / methanol / 2 h / 20 °C

7: 83 percent / pyridine / CHCl₃ / 16 h / 20 °C

8: 59 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 8: Swern oxidation;

DOI:10.1021/ol048459b

Reference yield:

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate (895558-57-3) → 1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-xylulose (786709-74-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.36 g / tetrabutylammonium fluoride / tetrahydrofuran / 4 °C

2: sulfuric acid / 2 h / Heating

3: 1.28 g / NaH / dimethylformamide / 20 °C

4: 88 percent / hydrochloric acid / dioxane / Heating

5: 92 percent / NaBH₄ / methanol / 2 h / 20 °C

6: 83 percent / pyridine / CHCl₃ / 16 h / 20 °C

7: 59 percent / oxalyl chloride; dimethyl sulfoxide; diisopropylethylamine / CH₂Cl₂ / 0.17 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 7: Swern oxidation;

DOI:10.1021/ol048459b

upstream raw materials:

1-deoxy-1-fluoro-3,4-di-O-benzyl-5-O-benzoyl-D-lyxitol

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate

1-deoxy-1-fluoro-3,4-di-O-benzyl-D-lyxitol

Downstream raw materials:

Phosphoric acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester dimethyl ester

(2R,3S)-2,3-Bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propan-1-ol

Benzoic acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester