N-glycosylation with glycosyl diethyl phosphites: A highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides

DOI: 10.3987/COM-97-S80

Source and publish data:

Heterocycles p. 215 - 220 (1997)

Update date:2022-09-26

Topics:

Authors:

Hashimoto, Shun-Ichi

Inagaki, Jun

Sakamoto, Hiroki

Sano, Ai

Nakajima, Makoto

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Article abstract of DOI:10.3987/COM-97-S80

A facile and direct method for the construction of 2′-deoxy-β-N-glycosidic linkages in 2′-deoxyribonucleoside synthesis has been developed by using 3-(3,4,5-trimethoxybenzoyl)-protected 2-deoxyribofuranosyl diethyl phosphites as a glycosyl donor in the presence of trimethylsilyl triflate, wherein coupling reactions with silylated pyrimidine bases have been found to exhibit β-selectivities up to 96%.

Full text of DOI:10.3987/COM-97-S80

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