84245-11-4

Basic information

• Product Name: Ganciclovir
• Synonyms: Methanol,[2-(phenylmethoxy)-1-[(phenylmethoxy)methyl]ethoxy]-, acetate (9CI); 1,3-Dibenzyloxy-2-acetoxymethoxypropane
• CAS NO: 84245-11-4
• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.4
• Mol File: 84245-11-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ganciclovir(CAS DataBase Reference)
• NIST Chemistry Reference: Ganciclovir(84245-11-4)
• EPA Substance Registry System: Ganciclovir(84245-11-4)

Safety Data

• Hazardous Substances Data: 84245-11-4(Hazardous Substances Data)

Upstream product

• 75-09-2 dichloromethane 
• 4382-76-7 methoxymethyl acetate 
• 59991-89-8 1,2-dibenzylpropanetriol 
• 7732-18-5 water 
• 104-15-4 toluene-4-sulfonic acid 
• 74564-16-2 1,3-dibenzyloxy-2-(chloromethoxy)propane 
• 100-51-6 benzyl alcohol 
• 6972-79-8 dibenzyl glycerol 
• 127-08-2 potassium acetate 

Downstream Products

• 84222-48-0 N²-acetyl-7-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine 
• 82410-30-8 N²-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine 
• 273410-26-7 4-iodo-3-methoxycarbonyl-1-{[1,3-bis(benzyloxy)-2-propoxy]methyl}-pyrazole 
• 101924-22-5 2-Amino-8-(2-benzyloxy-1-benzyloxymethyl-ethoxymethyl)-8H-imidazo[1,2-a][1,3,5]triazin-4-one 
• 101924-21-4 2-acetamido-8-<(1,3-dibenzyloxy-2-propoxy)methyl>imidazo<1,2-a>-s-triazin-4-one 
• 93503-26-5 1-((1,3-bis(benzyloxy)-2-propoxy)methyl)-2-thiouracil 
• 116457-85-3 1-((1,3-bis(benzyloxy)-2-propoxy)methyl)-2-thiopyrimidine 

Relevant articles and documents

Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent

Compounds useful as antiviral agents are defined by the following formula: STR1 and the pharmaceutically acceptable acid addition salts thereof wherein R1 is hydrogen or --C(O)R7 wherein R7 is hydrogen, alkyl of one to nineteen carbon atoms, hydroxyalkyl of one to eight carbon atoms, alkoxyalkyl of two to nine carbon atoms, alkenyl of two to nineteen carbon atoms, phenyl, 1-adamantyl or 2-carboxyethyl and the pharmaceutically acceptable alkali metal salts thereof; R2 is --C(O)R7 wherein R7 is as defined above; R3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR9 R10 wherein R9 and R10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R8 wherein R8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR9 R10 wherein R9 and R10 are as defined above or --NHC(O)R8 wherein R8 is as defined above and R4 together with R5 is a bond; or (b) R5 together with R6 is a keto group and R4 is hydrogen.

Alkoxy methyl ether and alkoxy methyl ester derivatives

Intermediates and methods for producing intermediates for use in preparing 9-(1,3-dihydroxy-2-propoxymethyl)-guanine and esters and ethers thereof.

Process for the preparation of acylals

Compounds of the formula STR1 can advantageously be prepared by reacting compounds the formula II STR2 in which the substituents R1 -R4 have the meanings given, with the anhydride of the formula III STR3 in the presence of dimethyl sulfoxide and the acid corresponding to the anhydride of the formula III.

Process for preparing guanine derivatives

1-Monophosphate esters, 1,3-bisphosphate esters and cyclic phosphate esters of 9-(1,3-dihydroxy-2-propoxymethyl)guanine are useful as antiviral agents.

9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent

The compound 9-(1,3-dihydroxy-2-propoxymethyl)guanine and the pharmaceutically acceptable salts thereof are useful as antiviral agents.

9-[(1,3-dihydroxy-2-propoxy)methyl]guanine: A new potent and selective antiherpes agent

The synthesis of a new acyclic analogue of deoxyguanosine, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (DHPG, 1) is described starting from epichlorohydrin via condensation of 2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol (5) with N2,9-diacetylguanine (6). In vitro studies indicate that DHPG is a potent and broad-acting (herpes simplex virus types 1 and 2, cytomegalovirus, and Epstein-Barr virus) antiherpetic agent. In vivo studies indicate its lack of toxicity [LD50 (mice) = 1-2 g/kg, ip] and its superiority over acyclovir [oral ED50 = 7 (mg/kg)/day vs. 550 (mg/kg)/day in HSV-2 infected mice].

9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent

The compound 9-(1,3-dihydroxy-2-propoxymethyl)guanine and the pharmaceutically acceptable salts thereof are useful as antiviral agents.