Synthesis of chiral 3-substituted gamma-lactones and 9-furanosyladenine from (R)-2-(2,2-diethoxyethyl)-1,3-propanediol monoacetate prepared by lipase-catalyzed reaction.
A chiral building block, (R)-2-(2,2-diethoxyethyl)-1,3-propanediol monoacetate was synthesized in high optical and chemical yields by lipase-catalyzed transesterification. From this compound, we synthesized chiral 3-substituted gamma-lactones and a new nucleoside with antiviral activity.
Terao
Y
Y
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Akamatsu
M
M
Achiwa
K
K
D000241:Adenosine / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism*; D011409:Propylene Glycols / Q000737:chemistry*; D013237:Stereoisomerism
D000998:Antiviral Agents; D007783:Lactones; D011409:Propylene Glycols; C069875:2-(2,2-diethoxyethyl)-1,3-propanediol monoacetate; D008049:Lipase; D000241:Adenosine