On October 31, 2001, Tanaka, Kazuho; Yamano, Shinjiro; Mitsunobu, Oyo published an article.Application In Synthesis of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole The title of the article was Reductive ring opening of 6-deoxy-6-iodopyranosides and 5-deoxy-5-iodofuranosides by manganese. A convenient procedure for the preparation of chiral 5-hexenals and 4-pentenals. And the article contained the following:
Reaction of fully protected 6-iodopyranosides and 5-iodofuranosides with Mn in the presence of trimethylsilyl chloride and PbCl2 (Takai-conditions) afforded the corresponding 5-hexenals and 4-pentenals in good to moderate yields. For e.g., chiral hexenal I was prepared from D-glucopyranoside II in 79% yield via Mn-catalyzed reductive ring opening reaction. The chiral pentenals obtained from furanosides were unstable and hence, they were reduced with NaBH4 and were isolated as pentenols. Similarly, reductive ring opening of D-xylofuranoside III followed by reduction with NaBH4 gave chiral pentenol IV in 48% yield. 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).Application In Synthesis of (3aS,4S,6R,6aR)-4-(Iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole
The Article related to asym reductive ring opening pyranoside manganese catalyst, hexenal chiral preparation, pentenal chiral preparation, furanoside iodo deoxy reductive ring opening manganese catalyst, reductive ring opening pyranoside deoxy iodo manganese catalyst and other aspects.Application In Synthesis 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