Bicyclic nucleoside analogues from D-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives.
The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3'-O and 5'-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues.
Tripathi
Subhankar
S
Division of Medicinal Chemistry, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India.
Maity
Joy Krishna
JK
Achari
Basudeb
B
Mandal
Sukhendu B
SB
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003500:Cyclization; D005947:Glucose / Q000737:chemistry*; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D009705:Nucleosides; D005947:Glucose