2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose

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Cat Number

INT97614432

CAS Number

97614-43-2

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Product Detail Description Customer Q&A

CAS Number

97614-43-2

EINECS

619-281-1

Storage

Room temperature

Synonyms

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α- D-arabinof;InterMediate of Clofarabine;2-Fluoro-2deoxy-1,3,5-O-benzoyl-a-D-arabinofuranos

Molecular Formula

C26H21FO7

Molecular Weight

464.44

Smiles

JOAHVPNLVYCSAN-PPTKZWKYSA-N

Appearance

White to off-white powder

Melting Point

74-77℃

Boiling Point

584℃

Relative Density

1.35

General Description

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose is a fluorinated carbohydrate derivative featuring a fluorine atom at the C-2 position of a ribofuranose ring in which all three hydroxyl groups (at C-1, C-3, and C-5) are protected as benzoyl esters. The C-2 fluorine is metabolically stable (C-F bond is not cleaved in vivo) and locks the sugar ring in a specific conformation. The benzoyl protecting groups are removed by base-catalyzed hydrolysis after coupling to the nucleobase.

Mechanism of Action

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose is used as a key sugar donor in the synthesis of 2-fluoro-2-deoxynucleoside analogs. The C-2 fluorine atom prevents normal 2-OH-directed RNA conformation, blocking 2,5-phosphodiester bond formation and interfering with viral RNA-dependent RNA polymerase. The 2-fluoro substitution also increases the metabolic stability of the nucleoside toward phosphorolysis and nucleoside phosphorylases.

Application

2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose is used as a key intermediate in the synthesis of 2-fluoro-2-deoxynucleoside analogs, which are being developed as antiviral and anticancer agents. The 2-fluoroarabinose derivative is used in the synthesis of gemcitabine and clofarabine. It is also used in the synthesis of modified oligonucleotides (antisense oligonucleotides, siRNA) where the 2-fluoro modification increases nuclease resistance.

What is the recommended storage condition for 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

Is 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose compatible with common organic solvents used in pharmaceutical synthesis?

Solubility and compatibility information is available in the technical data sheet. For specific solvent compatibility questions, please contact our technical team.

What functional groups in 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Is 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-D-ribofuranose manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.