1270965-80-4

Basic information

• Product Name: (R_P,4'S_C)-2-(4'-benzyl-2'-N-cyanimino-oxazolidin-3'-yl)-4H-1,3,2-benzodioxaphosphorin-2-oxide
• Synonyms: (R_P,4'S_C)-2-(4'-benzyl-2'-N-cyanimino-oxazolidin-3'-yl)-4H-1,3,2-benzodioxaphosphorin-2-oxide
• CAS NO: 1270965-80-4
• Molecular Weight: 369.316
• Mol File: 1270965-80-4.mol

Chemical Properties

• CAS DataBase Reference: (R_P,4'S_C)-2-(4'-benzyl-2'-N-cyanimino-oxazolidin-3'-yl)-4H-1,3,2-benzodioxaphosphorin-2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R_P,4'S_C)-2-(4'-benzyl-2'-N-cyanimino-oxazolidin-3'-yl)-4H-1,3,2-benzodioxaphosphorin-2-oxide(1270965-80-4)
• EPA Substance Registry System: (R_P,4'S_C)-2-(4'-benzyl-2'-N-cyanimino-oxazolidin-3'-yl)-4H-1,3,2-benzodioxaphosphorin-2-oxide(1270965-80-4)

Safety Data

• Hazardous Substances Data: 1270965-80-4(Hazardous Substances Data)

Upstream product

• 90-01-7 salicylic alcohol 
• 3182-95-4 L-Phenylalaninol 
• 1270965-73-5 (S)-4-benzyl-2-(N-cyanimino)oxazolidine 
• 127164-51-6 2-chloro-4H-benzo[d][1,3,2]dioxaphosphinine 2-oxide 

Relevant articles and documents

Stereoselective synthesis and antiviral activity of methyl-substituted cycloSal-pronucleotides

Methyl-substituted cycloSal-pronucleotides of d4TMP were synthesized with high diastereoselectivities in satisfying chemical yields. The individual diastereomers were tested against HIV-1 and HIV-2 infected wild-type CEM/0 and HIV-2 infected thymidine kin

Diastereoselective synthesis of cyclosaligenyl-nucleosyl-phosphotriesters

A diastereoselective synthesis of cycloSal-phosphotriesters (cycloSal=cycloSaligenyl) based on chiral auxiliaries has been developed that allows the synthesis of single diastereomers of the cycloSal-pronucleotides. In previously described synthesis routes, the cycloSal-compounds were always obtained as 1:1 diastereomeric mixtures that could be separated in only rare cases. However, it was shown that the diastereomers have different antiviral activity, toxicity, and hydrolysis stabilities. Here, first a chiral thiazoline derivative was used to prepare nonsubstituted and 5-methyl-cycloSal- phosphotriesters in 48 and ≥95%a de (de=diastereomeric excess). However, this approach failed to give the important group of 3-substituted cycloSal-nucleotides. Therefore, two other chiral groups were discovered that allowed the synthesis of (RP)- and (SP)-3-methyl-cycloSal- phosphotriesters as well. The antiviral activity was found to be five- to 20-fold different between the two individual diastereomers, which proved the importance of this approach. Chiral chemical Trojan horses: cycloSal-nucleotides (cycloSal=cycloSaligenyl) of thymidine and cycloSal-pronucleotides of 3′-azido-3′-deoxythymidine (AZT) and 3′-deoxy-2′, 3′-didehydrothymidine (d4T) were prepared by a diastereoselective route for the first time by using a chiral auxiliary approach with up to ≥95%a de (see scheme). The procedure is suitable to synthesize cycloSal-phosphotriesters with different substitution patterns in the aromatic residue.