168786-98-9

Basic information

• Product Name: METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE
• Synonyms: METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE;Methyl-2,3-Dideoxy--Fluoro-5-O-(4-phenylbenzoyl)-Alpha-D-erythro-pentofuranoside;METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-;Methyl 2,3-dideoxy-3-fluoro-alpha-D-erythro-pentofuranoside 5-[1,1'-biphenyl]-4-carboxylate
• CAS NO: 168786-98-9
• Molecular Formula: C19H19FO4
• Molecular Weight: 330.3501632
• EINECS: -0
• Mol File: 168786-98-9.mol

Chemical Properties

• Appearance: /
• Density: 1.23±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• CAS DataBase Reference: METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE(168786-98-9)
• EPA Substance Registry System: METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE(168786-98-9)

Safety Data

• Hazardous Substances Data: 168786-98-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE is used as a potential antiviral and anticancer agent for its ability to inhibit key biological processes and pathways. Its interaction with nucleic acids and enzymes makes it a candidate for developing new therapeutics against viral infections and cancer.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE serves as a valuable compound for studying the structure-activity relationships of nucleoside analogs. This understanding can guide the design of more effective drugs with fewer side effects.
Used in Drug Development:
METHYL-2,3-DIDEOXY-3-FLUORO-5-O-(4-phenylbenzoyl)-ALPHA-D-ERYTHRO-PENTOFURANOSIDE is utilized in the development of prodrugs or drug candidates that can be metabolized into active pharmaceutical ingredients within the body. Its unique structure allows for targeted delivery and activation, potentially improving the efficacy and safety of treatments.

Upstream product

• 129468-49-1 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-threo-pentofuranoside 
• 125611-95-2 methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 
• 125611-99-6 methyl 2,3-dideoxy-5-O-(4-phenylbenzoyl)-β-D-glycero-pentofuranoside*0.25H2O 
• 129468-48-0 Methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-glyceropentofuranosid-3-ulose 
• 125611-96-3 Methyl 2-Deoxy-3-O-(methylsulfonyl)-5-O-(4-phenylbenzoyl)-α-D-erythro-pentofuranoside 

Downstream Products

• 168787-13-1 (E)-1-<2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-D-erythro-pentofuranosyl>-5-ethylidene-hydantoin 

Relevant articles and documents

A new approach for syntheses of 2′,3′-dideoxy-2′,3′ -dehydronucleosides using 2,2-difluoro-1,3-dimethylimidazolidine (DFI) as a dehydrating reagent

We found that 2,2-difluoro-1,3-dimethylimidazolidine (DFI) is useful for not only fluorination but also dehydrating reactions. This dehydrating ability of DFI was applied to the syntheses of dihydrofurans (2) that are possible starting materials for various anticancer or antiviral drugs.

Synthesis of hydantoin analogues of 3'-fluoro-3'-deoxythymidine (FLT)

Reaction of methyl 2-deoxy-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside 2 with diethylaminosulfur trifluoride (DAST) in a 1:10 molar ratio in CH2Cl2 at room temperature for 5 d afforded methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentafuranoside 4 in 57percent yield, while the α-anomer 3 under the same reaction conditions yielded the 3-fluoro-α-D-erythro derivative 10 in 14percent yield together with the 5-fluoro-D-α--threo derivative 11 in 22percent yield. (Z)-5-Benzylidene-, (E)-ethylidene- and 5,5-dimethylhydantoin nucleosides were obtained by condensation of the appropriate silylated nucleobases with 4.The protected nucleosides were in all cases deblocked by treatment with sodium methoxide in methanol.The (Z)-ethylidene group isomerized to the E configuration during the nucleoside synthesis. - Key words: hydantoin / 3'-fluoro-3'-deoxythymidine / methyl 2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranoside

Synthesis and Antivirial Evaluation of Quinazoline, Thieno/pyrimidine, and Lumazine Analogues of 3'-Fluoro-3'-deoxythymidine (FLT)

2,4(1H,3H)-Quinazolinediones 3a-c, lumazine (3d) and thienopyrimidine-2,4(1H,3H)-dione (8) were silylated and condensed with methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentafuranoside (2) by using trimethylsilyl triflate as a catalyst to afford the corresponding cyclic nucleosides 4 and 9 and acyclic nucleosides 5 and 10.Removal of the protecting group from the glycon moiety was achieved in good yields by treatment with sodium methoxide in methanol at room temperature.The new FLT analogues were devoid of activity against HIV-1 and HSV-1. - Keywords: Nucleosides / HIV / 3'-Fluoronucleosides / FLT analogues

A Short Route to 3'-Deoxy-3'-fluorothymidine

The 5-OH protected methyl glycosides 2 and 3 were epimerized to give the corresponding epimers 6 and 7 via an oxidation-reduction procedure.Reaction of 6 with diethylaminosulfur trifluoride (DAST) afforded the fluoro sugar 8, which was coupled with thymine to give 3'-deoxy-3'-fluorothymidine (12) after deprotection with saturated ammonia in methanol.