On December 4, 1981, Ariatti, Mario; Zemlicka, Jiri published an article.Quality Control of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole The title of the article was Reaction of carbohydrate halides with magnesium. Novel carbon-carbon coupling of sugar derivatives via organometallic intermediates. And the article contained the following:
The reaction of 3-deoxy-3-C-(iodomethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (I) with sublimed Mg in refluxing THF gave dimer II and only traces of the 3-deoxy-3-Me derivative Similarly, Me 5-deoxy-5-iodo-2,3-O-isopropylidene-β-D-ribofuranoside (III) afforded the 5-5′-coupled compound, and 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose yielded the 6-6′-joined derivative The interaction of I with III gave the unsym. product in addition to the corresponding 2 sym. dimers. Dimer formation was also predominant in reaction of I with Mg in the presence of compounds such as PhCN or N-phthaloyl-L-phenylalanine 2-pyridine-2-thiol ester, which otherwise effectively trap the Grignard reagents. 5′-Deoxy-5′-iodo-2′,3′-O-isopropylidene-N3-methyluridine (IV) gave neither dimer nor the Grignard reagent. In addition, the dimer formation from I was inhibited in the presence of IV. II resulted also from the reaction of I with BuLi in THF whereas the interaction of the bromo analog of I produced only the 3-deoxy derivative The experimental process involved the reaction of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole(cas: 38838-06-1).Quality Control of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
The Article related to grignard coupling sugar halide, dimerization sugar, Carbohydrates: Monosaccharides, Glycals and other aspects.Quality Control of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem