Synthesis of acyclic nucleoside derivatives
View Patent ↗Methods and novel intermediates for the preparation of acyclic nucleoside derivatives of the formula: where one of R 1 and R 2 is an amino acid acyl group and the other of R 1 and R 2 is a —C(O)C 3 -C 21 saturated or monounsaturated, optionally substituted alkyl and R 3 is OH or H; or a pharmaceutically acceptable salt thereof.
1. A compound of the formula:
wherein R 6 and R 7 are lower alkyl or R 6 and R 7 taken together are —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 —, R 8 is C 1 -C 21 saturated or monounsaturated, optionally substituted alkyl.
2. The compound of claim 1 wherein R 6 and R 7 are —CH 3 or —CH 2 CH 3 or R 6 and R 7 taken together are —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 — and R 8 is CH 3 .
3. The compound of claim 1 wherein R 6 and R 7 are —CH 2 CH 3 and R 8 is CH 3 .
4. The compound of claim 1 wherein R 6 and R 7 are —CH 3 or —CH 2 CH 3 or R 6 and R 7 taken together are —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 — and R 8 is —(CH 2 ) 16 CH 3 .
5. The compound of claim 1 wherein R 6 and R 7 are —CH 2 CH 3 and R 8 is —(CH 2 ) 16 CH 3 .
6. A compound of the formula:
wherein R 8 is C 1 -C 21 saturated or monounsaturated, optionally substituted alkyl and R 12 is —CH(Ph) 2 , —C(Ph) 3 or —Si(t-Bu)(CH 3 ) 2 wherein Ph is phenyl.
7. The compound of claim 6 wherein R 8 is CH 3 and R 12 is as defined therein.
8. The compound of claim 6 wherein R 8 is —(CH 2 ) 16 CH 3 and R 12 is as defined therein.
9. A compound of the formula:
wherein R 10 is C 3 -C 21 saturated or monounsaturated, optionally substituted alkyl, R 11 is isopropyl or isobutyl and P 1 is an N-protecting group.
10. The compound of claim 9 wherein R 10 is CH 3 (CH 2 ) 16 —, R 11 is isopropyl and P 1 is benzyloxycarbonyl, t-butyloxycarbonyl or allyloxycarbonyl.
11. The compound of claim 9 wherein R 10 is CH 3 (CH 2 ) 16 —, R 11 is isopropyl and P 1 is benzyloxycarbonyl.