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US 5,329,008 AGranted
Synthesis of a 3,4-dihydroxy-1-cyclopentanylpurinone
AssigneeGlaxo Inc.
InventorsJohn J. Partridge, Brian L. Bray
Life of this patent
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Abstract
Synthesis of the triol of the following formula (I) from an alcohol of the formula (IV): ##STR1## via steps including protecting and then cyanating the alcohol to yield a cyanide, isomerization of the double bond, hydrolysis followed by reduction of the cyanide back to an alcohol and cis-dihydroxylation of the double bond.
Claims13
A method of synthesizing a triol of the following formula (I):
- ##STR11## or an acid- or base-addition salt thereof, which comprises the steps of:
- i) reacting a cyclopentene of the following formula (II):
- ##STR12## wherein R is C.sub.1-6 alkyl or OC.sub.1-6 alkyl, with a purine of the following formula (III):
- ##STR13## to yield an alcohol of the following formula (V):
- ##STR14## wherein Pro is an amino protecting group, ii) cyanating the alcohol of formula (V) to yield the cyanide of the following formula (VIII):
- ##STR15## iii) deprotecting, hydrolyzing, and then reducing the cyanide of formula (VIII) to yield the monoalcohol of the following formula (X):
- ##STR16## iv) performing a cis-dihydroxylation on the monoalcohol of formula (X) to produce the triol of formula (I).
4 more elements
A method of synthesizing a cyanide of the following formula (VIII):
- ##STR20## wherein Pro is an amino protecting group, which comprises the steps of:
- a) sulfonating an alcohol of the following formula (V):
- ##STR21## with a sulfonating reagent to yield a compound of the following formula (VI):
- ##STR22## wherein R.sup.1 is CH.sub.3 or H.sub.3 CC.sub.6 H.sub.4 ;
- and b) displacing the sulfonyl moiety with a nitrile moiety to yield the cyanide of formula (VIII).
2 more elements
Dependencies are inferred from the claim text.