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Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28
Graphical Abstract
Figure 1: Retrosynthetic pathway for the synthesis of the target carbocyclic nucleoside methylphosphonates.
Scheme 1: Reagents and conditions: (a) (CH3O)2P(O)CH3, n-BuLi, THF, −78 °C/rt, 2 h, 63%; (b) H2, Pd/C, MeOH, ...
Scheme 2: Reagents and conditions: (a) N6-bis-Boc-adenine or 2-amino-6-chloropurine, PPh3, DIAD, THF, 0 °C to...
Scheme 3: Reagents and conditions: (a) N6-bis-Boc-adenine, PPh3, DIAD, THF, rt, 56%; (b) TFA, Cl(CH2)2Cl, rt,...
Figure 2: Numbering for 14 and 16.
Figure 3: Selected NOESY correlations for compound (+/−)-16.
Scheme 4: Reagents and conditions: (a) i) Boc2O, DMAP, THF, rt; ii) K2CO3, MeOH, 75%; (b) PPh3, DIAD, THF, rt...
Scheme 5: Reagents and conditions: (a) N6-Bz-adenine or 2-amino-6-chloropurine, PPh3, DIAD, THF, 0 °C to rt, ...