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. 2021 Dec 15;87(6):3895–3909. doi: 10.1021/acs.joc.1c01812

Table 1. Solid-Phase Synthesis of TPST Dimer.

  condensation conditions
    
entry condensing reagents base (0.6 M) chemoselectivity (PO:PS)a HPLC yield (%)b
1 BOMP 2,6-lutidine   <1
2 MNTP 2,6-lutidine 6:94 91
3 PyNTP 2,6-lutidine 4:96 94
4 PyNTP pyridine 3:97 94
5 PyNTP quinoline 2:98 94
6 PyNTP quinolinec 3:97 95
7 PyNTP   1:99 97
a

Determined by RP-HPLC: area ratio of TPST and TPOT.

b

Determined by RP-HPLC: area ratio of TPST/(TPST + TPOT + T).

c

1.8 M quinoline was used.