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

Base Information

Chemical Name:dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate
CAS No.:850144-22-8
Molecular Formula:C₂₂H₂₈FO₇P
Molecular Weight:454.432
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 6 articles about dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] 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: 69.0%

: 15205-57-9
tribenzyl phosphite

: 850144-21-7
(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-ol

: 850144-22-8
dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate

Guidance literature:: With pyridine; iodine; In dichloromethane; at -40 - 20 ℃;
DOI:10.1021/jo048022h

Reference yield:

: 73346-74-4
(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol

: 850144-22-8
dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / NaH / tetrahydrofuran / 3 h / 20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

3: 510 mg / NaH / dimethylsulfoxide / 20 °C

4: 47 percent / i-Pr₂NH*3HF / 19 h / 100 °C

5: 95 percent / H₂ / Pd/C / ethanol / 3 h / 20 °C

6: 69 percent / I₂; pyridine / CH₂Cl₂ / -40 - 20 °C

With pyridine; hydrogen; iodine; sodium hydride; Dess-Martin periodane; fluorhydrate de diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 2: Dess-Martin oxidation;
DOI:10.1021/jo048022h

Reference yield:

: 78469-77-9
1-O-benzyl-2,3-O-isopropylidene-D-threitol

: 850144-22-8
dibenzyl [(3S,4R)-1-fluoro-2-hydroxy-3,4-(isopropylidenedioxy)pentan-5-yl] phosphate

Guidance literature:: Multi-step reaction with 5 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

2: 510 mg / NaH / dimethylsulfoxide / 20 °C

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

4: 95 percent / H₂ / Pd/C / ethanol / 3 h / 20 °C

5: 69 percent / I₂; pyridine / CH₂Cl₂ / -40 - 20 °C

With pyridine; hydrogen; iodine; sodium hydride; Dess-Martin periodane; fluorhydrate de diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; dimethyl sulfoxide; 1: Dess-Martin oxidation;
DOI:10.1021/jo048022h