151277-29-1

Basic information

• Product Name: Bis(4-propionyloxybenzyl) N,N-diisopropylphosphoramidite
• CAS NO: 151277-29-1
• Molecular Weight: 489.549
• Mol File: 151277-29-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Bis(4-propionyloxybenzyl) N,N-diisopropylphosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(4-propionyloxybenzyl) N,N-diisopropylphosphoramidite(151277-29-1)
• EPA Substance Registry System: Bis(4-propionyloxybenzyl) N,N-diisopropylphosphoramidite(151277-29-1)

Safety Data

• Hazardous Substances Data: 151277-29-1(Hazardous Substances Data)

Upstream product

• 921-26-6 N,N-diisopropylphosphoramide dichloride 
• 773873-35-1 4-(hydroxymethyl)phenyl propionate 

Relevant articles and documents

Synthesis, Bioactivity and Anti-HIV Activity of the Bis(4-acyloxybenzyl) and Mono(4-acylaoxybenzyl) Esters of the 5'-Monophosphate of AZT

To investigate the design of prodrugs of antiviral nucleosides for targeting to the central nervous system, the bis(4-acyloxybenzyl) esters of the 5'-monophosphate of AZT 5 (R = Me, Et, Pri or But) have been prepared.The reaction of the appropriate bis(4-acyloxybenzyl) N,N-diisopropylphosphoramidite 10 (R = Me, Et, Pri or But) with AZT in the presence of 1H-tetrazole, followed by oxidation of the PIII intermediate with 3-chloroperoxybenzoic acid gave the required triesters 5 in good yield.The lithium salts of the mono(4-acycloxybenzyl) esters of the 5'-phosphate of AZT 7 (R = Me, Et, Pri or But) were prepared by treatment of the triesters 5 with lithium iodide.In the presence of porcine liver carboxyesterase the triesters 5 and diesters 7 decomposed readily to the 5'-monophosphate of AZT 9.The anti-HIV activities of the triesters 5 and diesters 7 were, with one exception, comparable to that of AZT, but the greater cytotoxicity of certain compounds in particular types of cell significantly reduced their selectivity indices.