Table 1.
5′▵ | 2 | 3′● | support | 5′ deprotection | activator, coupling time, efficiency | oxidation | 2′ deprotection | ref |
---|---|---|---|---|---|---|---|---|
TBDMS | DMT | CNEt | CPG | TCA | tetrazole, 6–12 min, >95% | I2a | i) fluoride (TBAF) | 24 |
Fpmp | DMT | CNEt | CPG | TCA | tetrazole, 3–15 min, >98% | I2a | ii) acid (NaOAc/pH 3.25) | 20 |
Nbn | DMT | CNEt | CPG | TCA | tetrazole, 5–15 min, ~95% | I2a | iii) hν8 nm) | 8 |
DTM | DMT | CNEt | CPG | TCA | ETT, 150 sec, >98% | I2a | iv) reduction (DTT or TCEP) | 21 |
allyl | DMT | allyl | ref. 53 | TCA | tetrazole, 12 min, >93% | t-C4H9OOH | i) metal Pd2(dba)3 | 22 |
TOM | DMT | CNEt | CPG | DCA | BTT, 2.5 min, >99% | I2a | i) fluoride(TBAF) | 26 |
ACE | BzH | Me | P | HF/TEA | ETT, 90 sec, >99% | t-C4H9OOH | ii) acid (HOAc/TEMED/pH 3.8) | 27 |
I2/H2O/THF/Pyr