1-deoxy-1-fluoro-D-xylulose-5-phosphate

Base Information

• Chemical Name: 1-deoxy-1-fluoro-D-xylulose-5-phosphate
• CAS No.: 786709-64-6
• Molecular Formula: C₅H₁₀FO₇P
• Molecular Weight: 232.102
• Mol file: 786709-64-6.mol

Synonyms:

Chemical Property of 1-deoxy-1-fluoro-D-xylulose-5-phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-deoxy-1-fluoro-D-xylulose-5-phosphate

There total 13 articles about 1-deoxy-1-fluoro-D-xylulose-5-phosphate 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:

Phosphoric acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester dimethyl ester (786709-78-2) → 1-deoxy-1-fluoro-D-xylulose-5-phosphate (786709-64-6,131612-92-5)

Guidance literature:

Phosphoric acid (2R,3S)-2,3-bis-benzyloxy-3-(2-fluoromethyl-[1,3]dioxan-2-yl)-propyl ester dimethyl ester; With trimethylsilyl bromide; In chloroform-d1; for 1.5h;

With hydrogen; palladium on activated charcoal; In methanol; water; for 17h;

With hydrogenchloride; In water-d2; at 37 ℃; for 12h;

DOI:10.1021/ol048459b

Reference yield:

dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate (850144-22-8) → 1-deoxy-1-fluoro-D-xylulose-5-phosphate (786709-64-6,131612-92-5) + Phosphoric acid mono-((2R,3S)-5-fluoro-2,3,4,4-tetrahydroxy-pentyl) ester

Guidance literature:

dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate; With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

With hydrogen; palladium on activated charcoal; In tert-butyl alcohol; at 20 ℃; atmospheric pressure;

In water; for 120h; Title compound not separated from byproducts;

DOI:10.1021/jo048022h

Reference yield:

(3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether (850144-19-3) → 1-deoxy-1-fluoro-D-xylulose-5-phosphate (786709-64-6,131612-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 47 percent / i-Pr₂NH*3HF / 19 h / 100 °C

2.1: 95 percent / H₂ / Pd/C / ethanol / 3 h / 20 °C

3.1: 69 percent / I₂; pyridine / CH₂Cl₂ / -40 - 20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.2: H₂ / Pd/C / 2-methyl-propan-2-ol / 20 °C / atmospheric pressure

4.3: H₂O / 120 h

With pyridine; hydrogen; iodine; Dess-Martin periodane; fluorhydrate de diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; 4.1: Dess-Martin oxidation;

DOI:10.1021/jo048022h

upstream raw materials:

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

dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate

(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-ol

(3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether