183115-56-2

Basic information

• Product Name: (S)-1-[3,5-O-(2-benzyloxycarbonylamino-1-diethylphosphonoethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine
• Synonyms: (S)-1-[3,5-O-(2-benzyloxycarbonylamino-1-diethylphosphonoethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine
• CAS NO: 183115-56-2
• Molecular Weight: 553.506
• Mol File: 183115-56-2.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-[3,5-O-(2-benzyloxycarbonylamino-1-diethylphosphonoethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-[3,5-O-(2-benzyloxycarbonylamino-1-diethylphosphonoethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine(183115-56-2)
• EPA Substance Registry System: (S)-1-[3,5-O-(2-benzyloxycarbonylamino-1-diethylphosphonoethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine(183115-56-2)

Safety Data

• Hazardous Substances Data: 183115-56-2(Hazardous Substances Data)

Upstream product

• 814-49-3 diethyl chlorophosphate 
• 589-57-1 diethyl phosphorylchloridite 
• 214046-41-0 (R)-1-[3,5-O-(2-benzyloxycarbonylamino-1-ethoxyethylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine 
• 13347-35-8 ethyl N-benzyloxycarbonylamino-orthoacetate 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 

Relevant articles and documents

3',5'-O-phosphonoalkylidene derivatives of 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine: Synthesis and reactivity

Various 3',5'-O-(1-phosphonoalkylidene) derivatives of 1-(2-deoxy-β-D- threo-pentofuranosyl)thymine bearing a substituent in the ω-position of the alkylidene chain were prepared by the redox reaction of diethyl chlorophosphite with six-membered 3',5'-orthoesters of xylo-dT. Susceptibility of ω-haloalkylidene derivatives for nucleophilic substitution is discussed. The configuration of the final phosphonates was determined by 2D-ROESY NMR experiments.

Synthesis of Some Derivatives of 1-thymine Substituted in the ω-Position of the Alkylidene Moiety

Some ω-substituted derivatives of 1-thymine have been prepared.A key step in the synthesis is the reaction of chlorodiethylphosphite with cyclic 3',5'-O-(1-alkoxy)alkylidene nucleoside orthoesters bearing a substituent in the ω-position of the alkylidene moiety.