120362-28-9

Basic information

• Product Name: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol
• Synonyms: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol
• CAS NO: 120362-28-9
• Molecular Weight: 604.68
• Mol File: 120362-28-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol(120362-28-9)
• EPA Substance Registry System: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol(120362-28-9)

Safety Data

• Hazardous Substances Data: 120362-28-9(Hazardous Substances Data)

Upstream product

• 14347-83-2 (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 31618-90-3 diethyl (p-toluenesulfonyloxymethane)phosphonate 
• 120362-27-8 (R)-3-O-Benzyl-1-O-<(p-methoxyphenyl)diphenylmethyl>glycerol 
• 4799-67-1 3-O-benzylglycerol 
• 14347-83-2 1-O-benzyl-2,3-O-isopropylidene glycerol 
• 120362-27-8 1-Benzyloxy-3-[(4-methoxy-phenyl)-diphenyl-methoxy]-propan-2-ol 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 

Downstream Products

• 120362-34-7 [(R)-2-(4-Amino-pyrimidin-2-yloxy)-1-benzyloxymethyl-ethoxymethyl]-phosphonic acid diethyl ester 
• 120362-30-3 (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-(methylsulfonyl)glycerol 
• 120362-33-6 (S)-1-<3-(Benzyloxy)-2-<(diethylphosphonyl)methoxy>propyl>cytosine 
• 120362-29-0 (S)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>glycerol 
• 120362-34-7 [2-(4-Amino-pyrimidin-2-yloxy)-1-benzyloxymethyl-ethoxymethyl]-phosphonic acid diethyl ester 
• 120362-30-3 Methanesulfonic acid 3-benzyloxy-2-(diethoxy-phosphorylmethoxy)-propyl ester 
• 120362-29-0 (2-Benzyloxy-1-hydroxymethyl-ethoxymethyl)-phosphonic acid diethyl ester 

Relevant articles and documents

Synthesis and antiviral activity of the nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine

The acyclic nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cytosine (2, HPMPC) was prepared on a multigram scale in 18% overall yield starting from (R)-2,3-O-isopropylideneglycerol. The key step in the nine-step synthetic route is coupling of cytosine with the side-chain derivative 8 which bears a protected phosphonylmethyl ether group. In vitro data showed that HPMPC has good activity against herpes simplex virus types 1 and 2, although it was 10-fold less potent that acyclovir [ACV, 9-[(2-hydroxyethoxy)methyl]guanine]. By comparison, HPMPC exhibited greater activity than ACV against a thymidine kinase deficient strain of HSV 1 and was more potent than ganciclovir [DHPG, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine] against human cytomegalovirus. In vivo, HPMPC showed exceptional potency against HSV 1 systemic infection in mice, having an ED50 of 0.1 mg/kg per day (ip) compared with 50 mg/kg per day for ACV. HPMPc was also more efficacious than ACV in the topical treatment of HSV 1 induced cutaneous lesions in guinea pigs.