Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)
Publication type: Journal Article
Publication date: 1999-04-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl)butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N−9 alkylated product 26 which was isolated in 80% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2-amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2-dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
3
4
5
|
|
|
Tetrahedron
5 publications, 23.81%
|
|
|
Bioorganic and Medicinal Chemistry
2 publications, 9.52%
|
|
|
Journal of Organic Chemistry
2 publications, 9.52%
|
|
|
Canadian Journal of Chemistry
1 publication, 4.76%
|
|
|
Chemical and Pharmaceutical Bulletin
1 publication, 4.76%
|
|
|
Collection of Czechoslovak Chemical Communications
1 publication, 4.76%
|
|
|
Molecules
1 publication, 4.76%
|
|
|
Journal of Molecular Structure
1 publication, 4.76%
|
|
|
Magnetic Resonance in Chemistry
1 publication, 4.76%
|
|
|
Synthetic Communications
1 publication, 4.76%
|
|
|
Journal of Zhejiang University: Science A
1 publication, 4.76%
|
|
|
Progress in Heterocyclic Chemistry
1 publication, 4.76%
|
|
|
Asian Journal of Chemistry
1 publication, 4.76%
|
|
|
Synthesis
1 publication, 4.76%
|
|
|
1
2
3
4
5
|
Publishers
|
2
4
6
8
10
|
|
|
Elsevier
10 publications, 47.62%
|
|
|
American Chemical Society (ACS)
2 publications, 9.52%
|
|
|
Canadian Science Publishing
1 publication, 4.76%
|
|
|
Pharmaceutical Society of Japan
1 publication, 4.76%
|
|
|
Institute of Organic Chemistry & Biochemistry
1 publication, 4.76%
|
|
|
MDPI
1 publication, 4.76%
|
|
|
Wiley
1 publication, 4.76%
|
|
|
Taylor & Francis
1 publication, 4.76%
|
|
|
Zhejiang University Press
1 publication, 4.76%
|
|
|
Asian Journal of Chemistry
1 publication, 4.76%
|
|
|
Georg Thieme Verlag KG
1 publication, 4.76%
|
|
|
2
4
6
8
10
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
21
Total citations:
21
Citations from 2024:
0
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Brand B. et al. Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir) // Tetrahedron. 1999. Vol. 55. No. 16. pp. 5239-5252.
GOST all authors (up to 50)
Copy
Brand B., Reese C. B., Song Q., Visintin C. Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir) // Tetrahedron. 1999. Vol. 55. No. 16. pp. 5239-5252.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/s0040-4020(99)00169-6
UR - https://doi.org/10.1016/s0040-4020(99)00169-6
TI - Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)
T2 - Tetrahedron
AU - Brand, Briony
AU - Reese, Colin B.
AU - Song, Quanlai
AU - Visintin, Cristina
PY - 1999
DA - 1999/04/01
PB - Elsevier
SP - 5239-5252
IS - 16
VL - 55
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1999_Brand,
author = {Briony Brand and Colin B. Reese and Quanlai Song and Cristina Visintin},
title = {Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir)},
journal = {Tetrahedron},
year = {1999},
volume = {55},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/s0040-4020(99)00169-6},
number = {16},
pages = {5239--5252},
doi = {10.1016/s0040-4020(99)00169-6}
}
Cite this
MLA
Copy
Brand, Briony, et al. “Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9H-purine (famciclovir).” Tetrahedron, vol. 55, no. 16, Apr. 1999, pp. 5239-5252. https://doi.org/10.1016/s0040-4020(99)00169-6.