135086-58-7

Upstream product

• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 107-13-1 acrylonitrile 
• 139212-74-1 N-sodio-N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazidate 
• 138963-18-5 N'-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-4-toluenesulfonohydrazide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 138963-17-4 N'-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4-toluenesulfonohydrazide 

Relevant academic research and scientific papers

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, a

Glycosylidene carbenes: Part 3 - Synthesis of spirocyclopropanes

Thermolysis of the glycosylidene-derived O-benzylated diazirine 1 in the presence of N-phenylmaleimide (2), acrylonitrile (3), dimethyl fumarate (4), or dimethyl maleate (5) led in good yields to mixtures of the spirocyclopropanes 6/7, 8-11, 12/13, and 12/13/16/17. The diastereoselectivity depends upon the alkene. The cycloaddition of 1 to 5 is not diastereospecific, in keeping with previous results. Deprotection of 12, 13, 16, and 17 yielded the tetrols 14, 15, 18, and 19, respectively.