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Synthesis, Structure, and Conformation of 2′,3′‐Fused Oxathiane and Thiomorpholine Uridines
Author(s) -
Sun Jingbo,
Wu Jinchang,
Yang Hua
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790199
Subject(s) - chemistry , pyrimidine , intramolecular force , stereochemistry , hydroxymethyl , nucleoside , bicyclic molecule
The syntheses of two 2′,3′‐fused bicyclic nucleoside analogues, i.e. , 1‐[(4a R ,5 R ,7 R ,7a S )‐hexahydro‐5‐(hydroxymethyl)‐4,4‐dioxidofuro[3,4‐ b ][1,4]oxathiin‐7‐yl]pyrimidine‐2,4(1 H ,3 H )‐dione ( 1a ) and 1‐[(4a S ,5 R ,7 R ,7a S )‐hexahydro‐7‐(hydroxymethyl)‐1,1‐dioxido‐2 H ‐furo[3,4‐ b ][1,4]thiazin‐5‐yl]pyrimidine‐ 2,4(1 H ,3 H )‐dione ( 1b ), are described, the key step being an intramolecular hetero‐ Michael addition. Their structures and conformations, previously solved by X‐ray crystallography, were analyzed in more detail, using 1D‐ and 2D‐NMR as well as HR‐MS analyses.