CLXVIII.—Synthesis of amygdalin

Cyanogenic glycosides

“…An enzyme in snails (Giaja, 1919) acts on amygdalin to cleave the linkage between the cyanohydrin and sugar moieties and form gentiobiose. The structure of amygdalin was finally considered established in 1924 when Campbell and Haworth (1924) synthesized the cyanogen.…”

Recent Advances in the Chemistry of Cyanogenic Glycosides

“…Similarly, fully methylated gynocardin was found to be a hexamethyl derivative (29), furnishing a molecular ion (at m/e387) on electron impact. This was supported also by mass spectrometry.…”

“…4) Glycosides with an unsaturated, alicyclic aglycone (gynocardin type) (4), (17)· Most cyanogenic glycosides are simple glucosid~s, the only exceptions being amygdalin (I), lucumin (IS), and vicianin (6), which contain disaccharide residues. 29) JOR1SSEN and HAIRS (1891) (72,32) DUNSTAN and HENRY (1902) (38,82) POWER and GORNALL (1904) (92, 33, 4I , 44) BOURQUE LOT and DANJOU (1905) (20,53) a Compounds are arranged in chronological order according to the approximate date of their discovery.…”

“…The overall procedure normally consists of at least four steps (29,52,53). The product is subsequently converted into the corresponding amide which in turn is dehydrated to the desired nitrile.…”