2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one

Base Information

• Chemical Name: 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one
• CAS No.: 39809-25-1
• Molecular Formula: C10H15N5O3
• Molecular Weight: 253.261
• Mol file: 39809-25-1.mol

Synonyms:9-[4-Hydroxy-3-(hydroxymethyl)butyl]guanine;BRL 39123;Denavir;VSA 671;

Chemical Property of 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one

Chemical Property:

• Appearance/Colour: White crystalline solid
• Vapor Pressure: 5.81E-18mmHg at 25°C
• Melting Point: 275-277 °C
• Refractive Index: 1.748
• Boiling Point: 653.4 °C at 760 mmHg
• PKA: 14.42±0.10(Predicted)
• Flash Point: 348.9 °C
• PSA: 130.05000
• Density: 1.68 g/cm³
• LogP: -0.72610
• Storage Temp.: -20°C Freezer
• Solubility.: 0.02 M potassium phosphate: soluble2mg/mL

Purity/Quality:

99%min ^*data from raw suppliers

Penciclovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Description: Vectavir was launched in the UK for herpes labialis. Penciclovir is synthetically available by two routes of four steps each from 2- (hydroxymethyl)butane-l,4-diol and is active against HSV-1, HSV-2 VZV but has limited activity against CMV. Vectavir is an acyclic guanosine analog that acts as a competitive inhibitor of DNA polymerase. It is a metabolic product of famcyclovir that is preferentially phosphorylated by viral infected cells (by thymidine kinases) over normal cells. The triphosphate has a low activity against cellular DNA polymerase which is one possible explanation for its low toxicity. While its spectrum of activity is similar to acyclovir, it is longer acting because its triphosphate is 20 times more stable and is not metabolized.
• Uses: An antiviral. A deuterated version of Penciclovir, an antiviral
• Indications: Penciclovir has activity against HSV-1, HSV-2, VZV, and HBV. After oral administration, famciclovir is converted to penciclovir by first-pass metabolism. Penciclovir has a mechanism of action similar to that of acyclovir. It is first monophosphorylated by viral thymidine kinase; then it is converted to a triphosphate by cellular kinases.
• Therapeutic Function: Antiviral
• Clinical Use: Herpes zoster and genital herpes Orolabial herpes (topical) Penciclovir is approved as a topical formulation for the treatment of herpes labialis. In immunocompetent individuals, penciclovir shortens the duration of lesion presence and pain by approximately half a day when it is initiated within an hour of lesion development and applied every 2 hours during waking hours for 4 days.

Technology Process of 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one

There total 67 articles about 2-Amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3,9-dihydropurin-6-one 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%

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8) → Penciclovir (39809-25-1)

Guidance literature:

With hydrogenchloride; In water; for 3h; Time; Reflux; Industrial scale;

Reference yield: 92.6%

2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (172529-94-1) → Penciclovir (39809-25-1)

Guidance literature:

With formic acid; In water; Reagent/catalyst; Reflux;

Reference yield: 83.0%

6-chloro-9-[2-(2-phenyl-[1,3]dioxan-5-yl)-ethyl]-9H-purin-2-ylamine → Penciclovir (39809-25-1)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 3h;

DOI:10.1081/SCC-120026312

upstream raw materials:

⁽²⁾-amino-9-(4'-benzyloxy-3'-benzyloxymethyl)butyl-6-chloro-9H-purine

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

2-amino-6-chloro-9-<2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl>purine

2-amino-6-benzyloxy-9-<2'-(2,2-dimethyl-1,3-dioxan-5-yl)-ethyl>-9H-purine

Downstream raw materials:

N²-(p-anisyldiphenylmethyl)-9-[(4-(p-toluenesulfonyloxy))-3-p-anisyldiphenylmethoxy-methyl-butyl]guanine

Refernces

• 1、 -. "Preparation method of penciclovir". Paragraph 0041; 0048-0049. . Retrieved 2020/02/14.
• 2、 Torii, Takayoshi,Shiragami, Hiroshi,Yamashita, Keizo,Suzuki, Yumiko,Hijiya, Toyoto,Kashiwagi, Tatsuki,Izawa, Kunisuke. "Practical syntheses of penciclovir and famciclovir from N2-acetyl-7-benzylguanine". . p. 5709 - 5716. Retrieved 2007/10/03.