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Glycosylidene Carbenes Part 5 Synthesis of Glycono-1,5-lactone Tosylhydrazones as Precursors of Glycosylidene Carbenes
The benzyl- and the acyl-protected glyconolactone tosylhydrazones 6, 9, 12, 16, and 19 (Scheme 1) were prepared in good yields by treating the hemiacetals 4, 7, 10, 14, and 17 with N-tosylhydrazine, to give the N-glycosylhydrazines 5, 8, 11, 15, and 18, and by oxidizing these hydrazines with N-bromosuccinimide (NBS) in the presence of 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU), with CrO3-dipyridine complex or with pyridinium dichromate.Photolysis of the sodium salt 20 of 6 (Scheme 2) in the presence of N-phenylmaleimide, dimethyl fumarate, or acrylonitrile gave the corresponding cyclopropanes 21-28 in satisfactory yields.Photolytic or thermolytic glycosidation of phenol and 4-methoxyphenol by 20 yielded the anomeric glycosides 29/30 and 31/32, yields being marginally higher for the thermolytic process.Photolytic glycosidation of propan-2-ol gave the glycosides 33 and 34 in low yields only.Yields and ratios of products were compared to those obtained with the diazirine 1 as a source of glycosylidene carbenes.While the yields from 20 are lower, the ratios of products obtained in the photolytic reactions are in agreement with the formation of a common intermediate from both carbene precursors.
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics