146459-58-7

Basic information

• Product Name: (S)-2-[(diisopropoxyphosphoryl)methoxy]-3-fluoropropyl 4-methylbenzenesulphonate
• CAS NO: 146459-58-7
• Molecular Weight: 426.443
• Mol File: 146459-58-7.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-[(diisopropoxyphosphoryl)methoxy]-3-fluoropropyl 4-methylbenzenesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[(diisopropoxyphosphoryl)methoxy]-3-fluoropropyl 4-methylbenzenesulphonate(146459-58-7)
• EPA Substance Registry System: (S)-2-[(diisopropoxyphosphoryl)methoxy]-3-fluoropropyl 4-methylbenzenesulphonate(146459-58-7)

Safety Data

• Hazardous Substances Data: 146459-58-7(Hazardous Substances Data)

Upstream product

• 151223-08-4 (S)-1-O-benzyl-2-O-<(diisopropylphosphono)methyl>-3-fluoro-1,2-propanediol 
• 941293-48-7 (S)-3-(benzyloxy)-2-[(diisopropoxyphosphoryl)methoxy]propyl 4-methylbenzenesulphonate 
• 941293-70-5 diisopropyl (R)-((((1-benzyloxy)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate 
• 35717-98-7 bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate 
• 1305351-56-7 diisopropyl (S)-({[1-fluoro-3-(trityloxy)propan-2-yl]oxy}methyl)phosphonate 
• 146459-56-5 (S)-2-acetoxymethoxy-3-fluoropropyl p-toluenesulfonate 
• 146459-55-4 (S)-1-fluoro-2-methoxymethoxypropyl p-toluenesulfonate 
• 146459-54-3 (S)-3-fluoro-2-hydroxypropyl-4-methylbenzene sulfonate 
• 98-59-9 p-toluenesulfonyl chloride 
• 116-17-6 triisopropyl phosphite 

Downstream Products

• 146459-61-2 (S)-N⁶-benzoyl-9-(2-diisopropylphosphonylmethoxy-3-fluoropropyl)adenine 

Relevant articles and documents

Synthesis of fluorinated acyclic nucleoside phosphonates with 5-azacytosine base moiety

With respect to the strong antiviral activity of (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine various types of its side chain fluorinated analogues were prepared. The title compound, (S)-1-[3-fluoro-2-(phosphonomethoxy)propyl]-5-azacytosine

Synthesis and antiviral activity of N9-[3-fluoro-2- (phosphonomethoxy)propyl] analogues derived from N6-substituted adenines and 2,6-diaminopurines

An efficient method for the synthesis of N9-[3-fluoro-2- (phosphonomethoxy)propyl] (FPMP) derivatives of purine bases has been developed. Both (R)- and (S)-enantiomers of the N6-substituted FPMP derivatives of adenine and 2,6-diaminopurine were prepared and their anti-human immunodeficiency virus (HIV) and anti-Moloney murine sarcoma virus (MSV) activity was evaluated. Whereas none of the 6-substituted FPMPA derivatives showed any antiviral activity, several FPMPDAP derivatives had a moderate antiretroviral activity. Moreover, the data obtained from the study of the substrate activity of the active derivatives towards N6-methyl-AMP aminohydrolase support the notion that the studied N6-substituted FPMPDAP derivatives act as prodrugs of the antiretroviral FPMPG analogues.

SYNTHESIS OF N-(3-FLUORO-2-PHOSPHONOMETHOXYPROPYL) (FPMP) DERIVATIVES OF HETEROCYCLIC BASES

A new groupnof compounds has been prepared: N-(3-fluoro-2-phosphonomethoxypropyl) (FPMP) derivatives of purine and pyrimidine bases which exhibit a significant selective activity against a broad spectrum of retroviruses.Racemic N-(3-fluoro-2-phosphonomethoxypropyl) derivatives of adenine (V), guanine (IX), cytosine (XIII), 2,6-diaminopurine (XXI), 3-deazaadenine (XVII), xanthine (X) and hypoxanthine (VI) were prepared from the corresponding n-(3-fluoro-2-hydroxypropyl) derivatives after protection of amino group at the heterocyclic ring by selective benzoylation, reaction with diisopropyl p-toluenesulfonyloxymethylphosphonate (II), and subsequent removal of the protecting groups.Chiral FPMP derivatives were prepared by reaction of heterocyclic base with corresponding chiral synthon (XXX; XXXVII) followed by deprotection.The required chiral synthons were obtained from enantiomeric 3-fluoro-1,2-propanediols by two methods.In the first, the primary hydroxyl group was tritylated, the obtained derivative was reacted with compound II, the trityl group was removed and the product was mesylated to give synthon XXXVII.The second pathway considered tosylation of the primary hydroxyl group and conversion of the secondary hydroxyl into the acetoxymethyl ether via the methoxymethyl ether; treatment of the acetoxy compound with bromotrimethylsilane and triisopropyl phosphite afforded the desired synthon XXX.