627510-49-0

Basic information

• Product Name: [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester
• Synonyms: [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester
• CAS NO: 627510-49-0
• Molecular Weight: 475.484
• Mol File: 627510-49-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester(627510-49-0)
• EPA Substance Registry System: [(R)-2-(6-Benzoylamino-purin-9-yl)-1-methyl-ethoxymethyl]-phosphonic acid diisopropyl ester(627510-49-0)

Safety Data

• Hazardous Substances Data: 627510-49-0(Hazardous Substances Data)

Upstream product

• 35717-98-7 bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate 
• 160616-03-5 (R)-9-(2-hydroxypropyl)-N⁶-benzoyladenine 
• 98-88-4 benzoyl chloride 
• 160616-02-4 (R)-9-<2-(2-tetrahydropyranyloxy)propyl>adenine 

Downstream Products

• 147127-20-6 tenofovir 

Relevant articles and documents

SYNTHESIS OF ENANTIOMERIC N-(2-PHOSPHONOMETHOXYPROPYL) DERIVATIVES OF PURINE AND PYRIMIDINE BASES. I. THE STEPWISE APPROACH

The (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases (PMP derivatives) exhibit very high activity against retroviruses.This paper describes the synthesis of enantiomeric 9-(2-phosphonomethoxypropyl)adenines (I and XXVII), 9-(2-phosphonomethoxypropyl)-2,6-diaminopurines (II and XXXI), 9-(2-phosphonomethoxypropyl)guanines (III and XXIX) and 1-(R)-(2-phosphonomethoxypropyl)cytosine (XIX) by alkylation of N-protected N-(2-hydroxypropyl) derivatives of the corresponding bases with bis(2-propyl) p-toluenesulfonyloxymethylphosphonate (X), followed by stepwise N- and O-deprotection of the intermediates.The key intermediates, N-(2-hydropxypropyl) derivatives IX and XXV, were obtained by alkylation of the appropriate heterocyclic base with (R)- or (S)-2-(2-tetrahydropyranyloxy)propyl p-toluenesulfonate (VII or XXIII) ans acid hydrolysis of the resulting N- derivatives VIII and XXII.The chiral synthons were prepared by tosylation of (R)- or (S)-2-(2-tetrahydropyranyloxy)propanol (VI or XXI) available by reduction of enantiomeric alkyl 2-O-tetrahydropyranyllactates V and XXI with sodium bis(2-methoxyethyoxy)aluminum hydride.This approach was used for the synthsis of cytosine, adenine and 2,6-diaminopurine derivatives, while compounds derived from guanine were prepared by hydrolysis of 2-amino-6-chloropurine intermediates.Cytosine derivative IXe was also synthesized by alkylation of 4-methoxy-2-pyrimidone followed by ammonolysis of the intermediate IXf.