Refine
Has Fulltext
- no (1)
Year of publication
- 2019 (1)
Document Type
- Article (1)
Language
- English (1) (remove)
Is part of the Bibliography
- yes (1)
Institute
- Institut für Chemie (1) (remove)
The methoxymethyl-protected glycal L-amicetal, synthesized de novo from L-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an a-configured 6-desoxy-gliflozin derivative.