Tetrahedron Letters p. 225 - 228 (1998)
Update date:2022-08-03
Topics:
Hong, Joon H.
Chun, Byoung K.
Chu, Chung K.
Asymmetric synthesis of D-2',3'-dideoxy-2',3'-endo-methylene nucleosides was achieved via the intermediate 2,3-endo-methylene pentofuranoyl chloride 6, which was prepared from 1,2:5,6-Di-O-isopropylidene-D-mannitol 1 with high stereoselectivity (only α chlorosugar). The SN2 type condensation of 6 with sodium salt of adenine and silyated N4-benzoylcytosine gave the desired β-nucleosides as major isomers (β:α = 2.5:1 and 2:1, respectively).
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