Hydroformylation of 3,4-di-0-acetyl-~-xylal gave 4,5-di-0-acetyl-2,6-anhydro-3-deoxyaldehyde-D-lyxo-hexose (I) and 4,5-di-0-acetyl-2,6-a1~hydro-3-deoxy-uldehydo-~-xylo-hexose iII). llethyl sulfoxide oxidation of 2,3-di-0-acet~~1-1,5-anhydro-4-deoxy-~-u~ubino-hexitol (111) and of 2,3-di-0-acetyl-l,5-anhl-dro-L-xylo-hex (IV) yielded compoullds I and 11, respectively.Reaction of 3,4,6-tri-0-acetyl-D-glucal with carbon inonoxide and hydrogen under carefully controlled conditions yielded 4,5,7-tri-0-acetyl-2,6-anhydro-3-deoxy-uldehydo-~-~unno-heptose (VII) and 4 , . 5 , 7 -t r i -0 -a c e t y l -2 , 6 -a n h y d r o -3 -d e o x~c o -h e p t o s e (VIII) in a 707; yield. Compound V I I was readily separated from the mixture of aldoses and alditols by column chromatography. Alternatively, aldoses VII and VIII were separated via their P,4-dinitrophenylhydrazones. The co~lversio~l of aldoses \;I1 and VIII into their diethyl dithioacetal derivatives is also described.The fortnyl group located in an equatorial orientation was found t o be reduced a t a faster rate than its axial counterpart.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
hi@scite.ai
10624 S. Eastern Ave., Ste. A-614
Henderson, NV 89052, USA
Copyright © 2024 scite LLC. All rights reserved.
Made with 💙 for researchers
Part of the Research Solutions Family.