Hydrogenolysis of 3,5-0-benzylidene acetals with the LiAlH4-AlCl3 reagent in methyl d-xylofuranosides
✍ Scribed by András Lipták; András Neszmélyi; Pavol Kováč; Ján Hirsch
- Book ID
- 104204495
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 447 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
✦ Synopsis
Abebmt-The hydrogcnolysis of methyl 3,54benzylidene-a-and -/3-D-xylofuranoside derivatives with the LiAII&-AICI, reagent gave S-benzyl ethers as main products. In some cases the attack of the reagent occured at the ring oxygen of the furanoside skeleton to yield SObcnzyI-I-Omethylxylitol derivatives. The structure of the synthesized compounds was proved by %NMR spectroscopy. Unambiguous assignment of lies in the %NMR spectra of numerous partiauy methylrted methyl a-and &DxyIofuranoside derivatives has been made,
📜 SIMILAR VOLUMES
The active AlH2Cl reagent formed from equimolar quantitiee of AlC13 and LiAlH4, exhibits the properties of both Lewis acids and hydride donor&. Thia is the basis if its reactions with acetals to yield hydroxy-
Lanthanide-induced shifts in the 'H-n.m.r. spectra of the methyl 2,3-anhydro-4,6-0-benzylidene-D-hexopyranosides [manno (1 and 5), allo (2 and 6), gulo (3 and 7), Q! and 0, respectively, and wtalo (4)] have been measured. The observed shift data for the cx-manno, @-allo, and fl-gulo epoxides were i