214771-18-3

Upstream product

• 34051-37-1 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lacton 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Relevant academic research and scientific papers

Alkylidenation of sugar lactones and further transformation to C-glycosides

The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar δ-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated β-C-glycosides and amino β-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl2/NaBH4, affording the perbenzylated C-glycosides and amino β-C-glycosides. Other transformation of the enol ether function is also reported.

Stereocontrolled synthesis of β-C-glycosides and amino β-C-glycosides by Wittig olefination of perbenzylated glyconolactones derivatives

Wittig olefination of perbenzylated glyconolactones afforded stereoselectively the Z-C-glycosylidenes which were transformed to the corresponding β-C-glycosides and amino β-C-glycosides by hydrogenation followed by acetylation.