9-(2'-ACETOXYETHOXYMETHYL)-GUANINE

Base Information

• Chemical Name: 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE
• CAS No.: 102728-64-3
• Molecular Formula: C10H13N5O4
• Molecular Weight: 267.244
• Hs Code.: 2933599550
• Mol file: 102728-64-3.mol

Synonyms:9-(2-Acetoxyethoxymethyl)guanine;2-[(2-Amino-6-oxo-1, 6-dihydro-9H-purin-9-yl)methoxy]ethyl acetate;

Chemical Property of 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE

Chemical Property:

• Melting Point: 242-244°C (dec.)
• Boiling Point: 565.4 °C at 760 mmHg
• PKA: 9.34±0.20(Predicted)
• Flash Point: 295.7 °C
• PSA: 125.12000
• Density: 1.61 g/cm³
• LogP: -0.17980
• Storage Temp.: Refrigerator

Purity/Quality:

99% ^*data from raw suppliers

AcyclovirAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 68
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Acyclovir (A192400) impurity.

Technology Process of 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE

There total 23 articles about 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3)

Guidance literature:

With triethylamine; In ethanol; for 10h; Heating;

DOI:10.1055/s-1990-26904

Reference yield: 95.0%

acycloguanosine (59277-89-3) + acetic anhydride (108-24-7) → 9-[(acetoxyethoxy)methyl]guanine (102728-64-3)

Guidance literature:

With dmap; In dimethyl sulfoxide; for 0.166667h; Inert atmosphere;

DOI:10.1248/cpb.59.1089

Reference yield: 94.0%

acetic anhydride (108-24-7) + acyclovir sodium salt → 9-<(2-acetoxyethoxy)methyl>guanine (102728-64-3)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1002/hlca.19890720811

upstream raw materials:

2-amino-1,9-dihydro-6H-purin-6-one

2-acetoxyethyl acetoxymethyl ether

1,1,1,3,3,3-hexamethyl-disilazane

6-Trimethylsilanyloxy-9H-purin-2-ylamine

Downstream raw materials:

9-[(2-acetoxyethoxy)methyl]-2-N-[N-(benzyloxycarbonyl)-valyl-prolyl]guanine

Acetic acid 2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-ethyl ester

2-((2-amino-6-(benzyloxy)-9H-purin-9-yl)methoxy)ethyl acetate

2-((2-amino-6-(benzyloxy)-9H-purin-9-yl)methoxy)ethanol

Refernces

• 1、 Madre, M. A.,Zhuk, R. A.,Lidak, M. Yu.. "ANALOGS OF PURINE NUCLEOSIDES. I. STUDIES ON METHODS OF SYNTHESIS OF 9-GUANINE - ACYLOGUANOSINE". . p. 806 - 809. Retrieved 1985.
• 2、 De Regil-Hernandez, Ruben,Martinez-Lagos, Fernando,Rodriguez-Bayon, Amalia,Sinisterra, Jose-Vicente. "New green synthesis and formulations of acyclovir prodrugs". . p. 1089 - 1093. Retrieved 2011.
• 3、 Stimac,Kobe. "A new synthesis of acyclovir prodrugs. N2-acetylacyclovir and 6-deoxyacyclovir". . p. 461 - 464. Retrieved 1990.
• 4、 Khalymbadzha, Igor A.,Shestakova, Tatyana S.,Subbotina, Julia O.,Eltsov, Oleg S.,Musikhina, Alexandra A.,Rusinov, Vladimir L.,Chupakhin, Oleg N.,Karpenko, Inna L.,Jasko, Maxim V.,Kukhanova, Marina K.,Deev, Sergey L.. "Synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a] pyrimidin-7-ones by one-step Vorbrüggen glycosylation". . p. 1298 - 1305. Retrieved 2014/02/14.
• 5、 Sautrey, Guillaume,Clarot, Igor,Rogalska, Ewa,Regnouf-De-Vains, Jean-Bernard. "New potential prodrugs of aciclovir using calix[4]arene as a lipophilic carrier: Synthesis and drug-release studies at the air-water interface". . p. 2060 - 2069. Retrieved 2013/02/25.