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• W2050065631 abstract "Methyl α-l- and α-d-glucopyranodsides have been synthesized from mehtyl (R)- and (S)-(2-furyl)glycolates (3), respectively. The key intermediates, methyl 6-O-benzyl-2,3-dideoxy-l(and d)-hex-2-enopyranosid-4-uloses (13), were obtained in the seven steps from the ester 3, without change of configuration of the asymmetric center, which became C-5 in the sugar molecule. Reduction of the ketone group at C-4 in the glycoside 13 with sodium borohydride afforded the corresponding methyl 6-O-benzyl-2,3-dideoxy-erythro-hex-2-enopyranosides (14). Epoxidation of the double bond in 14, followed by oxirane ring-opening in the anhydro sugar 16, and subsequent catalytic hydrogenolysis of the benzyl group led to the title compounds." @default.
• W2050065631 created "2016-06-24" @default.
• W2050065631 creator A5001256318 @default.
• W2050065631 creator A5005490254 @default.
• W2050065631 date "1977-05-01" @default.
• W2050065631 modified "2023-09-27" @default.
• W2050065631 title "Stereoselective total synthesis of methyl α-d- and α-l-glucopyranosides" @default.
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• W2050065631 doi "https://doi.org/10.1016/s0008-6215(00)84452-3" @default.
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