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Purification of 9N-[(1′R,3′R)-trans-3′-hydroxycyclopentanyl]adenine HCl: a combination of theory and experiment

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
53
Issue
21
Identifiers
DOI: 10.1016/s0040-4020(97)00421-3

Abstract

Abstract This paper describes the preparation of 9 N-[(1′ R,3′ R)- trans-3′-hydroxycyclopentanyl]adenine ( 1), 3 N-[(1′ R,3′ R)- trans-3′-hydoxycyclopentanyl]adenine ( 2) and 7 N-[(1′ R,3′ R)- trans-3′-hydroxycyclopentanyl]adenine ( 3). Calculations and titrations to predict and determine the basicity of 1, 2 and 3 are also disclosed. A method was devised to purify a mixture of silyl ethers 4, 5 and 6 via an acid wash (to remove 5; as supported by calculations and titrations) followed by recrystallization of 4 (to remove 6). Subsequent desilylation of 4 gives desired 1.

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