Rapid access to 1,6-anhydro-beta-L-hexopyranose derivatives via domino reaction: synthesis of L-allose and L-glucose.
An expeditious and efficient synthesis of 1,6-anhydro-beta-L-hexopyranosyl derivatives 3 as valuable building blocks for the preparation of L-sugars is herein reported. This route relies upon the use of a domino reaction involving five synthetic steps from the 5,6-dihydro-1,4-dithiin 4. As 1,6-anhydro derivatives 3 are obtained, dithioethylene bridge removal and double-bond dihydroxylation give access to protected L-allose and L-glucose in stereoselective fashion and high yields.
D'Alonzo
Daniele
D
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II-Complesso Universitario Monte Sant'Angelo via Cinthia, 4 I-80126 Napoli, Italy.
Guaragna
Annalisa
A
Napolitano
Carmela
C
Palumbo
Giovanni
G
D005030:Ethylenes / Q000737:chemistry; D005947:Glucose / Q000138:chemical synthesis* / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013997:Time Factors
D005030:Ethylenes; D013438:Sulfhydryl Compounds; C002055:allose; D006859:Hydrogen; C036216:ethylene; D005947:Glucose