On September 6, 2000, Hyldtoft, Lene; Madsen, Robert published an article.Recommanded Product: (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole The title of the article was Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis. And the article contained the following:
A general method for carbocyclization of carbohydrates is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction, Me ω-deoxy-ω-iodo glycosides undergo reductive elimination with zinc to produce a terminal double bond. This also liberates the aldehyde which is immediately alkylated in situ by various organozinc reagents. The alkylation occurs under Barbier conditions with methylene iodide and several allyl bromides. Zinc plays a dual role by both promoting the reductive elimination and activating the alkyl halide. Vinylation is carried out by adding divinylzinc. When a new stereogenic center is generated, moderate to excellent stereocontrol is generally observed An amino group can be introduced by trapping the intermediate aldehyde as an imine prior to the alkylation. The reductive elimination-allylation sequence can also be promoted by indium metal. All the alkylations produce a second double bond, and the obtained dienes are subsequently subjected to ring-closing olefin metathesis to produce the corresponding carbocycles. A newly developed catalyst with an N-heterocyclic carbene ligand is more reactive toward these carbohydrate-derived dienes than com. available Grubbs catalyst. Acetylation of the free hydroxy groups improves the metathesis reaction significantly. Both five- and six-membered carbocycles are available by this route, including a number of conduritols and quercitols. 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).Recommanded Product: (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
The Article related to domino reaction cyclitol preparation cyclization, cyclitol preparation cyclization barbier reductive elimination, alditol diene catalyzed cyclization cyclitol preparation and other aspects.Recommanded Product: (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