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. 2021 Jun 29;12(10):1680–1689. doi: 10.1039/d1md00079a

Yields for protected triazoles 12a–g from the copper azide-alkyne cyclisation coupling of 5′-O-propargyluridine (8) and α-azidophosphonates (11a–g), followed by their deprotection to form the final deprotected 1,2,3-triazole series in their Na+ salt form (13a–g).

R1 Click yield (R2: OBn)a Deprotection yield (R2: ONa+)b
graphic file with name d1md00079a-u1.jpg 12a: 51% 13a-(s): 99%
13a-(l): 91%
graphic file with name d1md00079a-u2.jpg 12b: 52% 13b-(s): 94%
13b-(l): 99%
graphic file with name d1md00079a-u3.jpg 12c: 66% 13c-(s): 97%
13c-(l): 91%
graphic file with name d1md00079a-u4.jpg 12d: 57% 13d-(s): 92%
13d-(l): 62%
graphic file with name d1md00079a-u5.jpg 12e: 60% 13e-(s): 92%
13e-(l): 85%
graphic file with name d1md00079a-u6.jpg 12f: 52% 13f-(s): 95%
13f-(l): 92%
graphic file with name d1md00079a-u7.jpg 12g: 57% 13g-(s): 96%
13g-(l): 92%
a

Yield of corresponding 1,2,3-triazole linked product from CuAAC click coupling (12a–g, Scheme 2).

b

Yield of final compound after catalytic hydrogenation deprotection and RP-HPLC separation and purification of diastereomers (13a–g, Scheme 2).