Desacetyl Famciclovir

Base Information

• Chemical Name: Desacetyl Famciclovir
• CAS No.: 104227-88-5
• Molecular Formula: C₁₂H₁₇N₅O₃
• Molecular Weight: 279.299
• Hs Code.: 2933599550
• UNII: NE5144EK4H
• DSSTox Substance ID: DTXSID60434620
• ChEMBL ID: CHEMBL881
• Mol file: 104227-88-5.mol

Synonyms:Desacetyl Famciclovir;104227-88-5;9-[4-acetoxy-3-(hydroxymethyl)but-1-yl]-2-aminopurine;120687-07-2;MONO-DESACETYL FAMCICLOVIR;[4-(2-aminopurin-9-yl)-2-(hydroxymethyl)butyl] Acetate;BRL 43594;NE5144EK4H;4-(2-amino-9h-purin-9-yl)-2-(hydroxymethyl)butyl acetate;2-(2-(2-Amino-9H-purin-9-yl)ethyl)-3-hydroxypropyl acetate;2-[2-(2-amino-9H-purin-9-yl)ethyl]-3-hydroxypropyl acetate;1,3-Propanediol, 2-(2-(2-amino-9H-purin-9-yl)ethyl)-, 1-acetate;CHEMBL881;UNII-NE5144EK4H;SCHEMBL1878763;DTXSID60434620;OUMGIMAEASXOJH-UHFFFAOYSA-N;2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol 1-Acetate;MFCD08063728;MONOACETYL-6-DEOXY PENCICLOVIR;AKOS030255718;AS-69250;CS-0196471;FT-0665920;D80603;J-001135;9-(4-acetoxy-3-hydroxymethylbut-1-yl)-2-aminopurine

Chemical Property of Desacetyl Famciclovir

Chemical Property:

• Melting Point: 166-168℃
• Boiling Point: 525.0±60.0 °C(Predicted)
• PKA: 14.62±0.10(Predicted)
• PSA: 116.15000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: 0.55140
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 279.13313942
• Heavy Atom Count: 20
• Complexity: 330

Purity/Quality:

98% ^*data from raw suppliers

DesacetylFamciclovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)CO
• Uses: A metabolite of Famciclovir (F101125).

Technology Process of Desacetyl Famciclovir

There total 7 articles about Desacetyl Famciclovir 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: 95.0%

Trimethyl orthoacetate (1445-45-0) + 6-deoxypenciclovir (104227-86-3) → (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine (120687-07-2,104227-88-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0968-0896(99)00086-3

Reference yield: 89.7%

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8) → 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4) + (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine (120687-07-2,104227-88-5)

Guidance literature:

With water; ammonium formate; palladium on charcoal; In ethyl acetate; at 50 ℃; for 5h; Product distribution / selectivity;

Reference yield: 64.0%

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8) → 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4) + 6-deoxypenciclovir (104227-86-3) + (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine (120687-07-2,104227-88-5)

Guidance literature:

With ammonium formate; palladium on charcoal; In methanol; acetic acid methyl ester; at 40 ℃; for 6.16667h; Product distribution / selectivity;

upstream raw materials:

9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Trimethyl orthoacetate

6-deoxypenciclovir

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

Downstream raw materials:

2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyloxybut-1-yl)purine

Refernces

• 1、 -. "PROCESS FOR PREPARING FAMCICLOVIR". Page/Page column 6-8. . Retrieved 2008/06/13.
• 2、 Kim, Dae-Kee,Lee, Namkyu,Ryu, Do Hyun,Kim, Young-Woo,Kim, Jae-Sun,Chang, Kieyoung,Im, Guang-Jin,Choi, Won-Son,Cho, Yong-Baik,Kim, Key H.,Colledge, Danni,Locarnini, Stephen. "Synthesis and evaluation of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines and 2-Amino-9-(3-alkoxycarbonyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir". . p. 1715 - 1725. Retrieved 2007/10/03.