Synthesis of novel d-2′, 3′-dideoxy-2′, 3′-endo-methylene nucleosides
JH Hong, BK Chun, CK Chu - Tetrahedron letters, 1998 - Elsevier
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).
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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