Derivatives of 5-deoxy-5-mercapto-d-glucose
β Scribed by M.S. Feather; Roy L. Whistler
- Publisher
- Elsevier Science
- Year
- 1962
- Tongue
- French
- Weight
- 98 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
IN the course of syntheses of sugars wherein the ring oxygen atom is replaced with another hetero atom,2 the sulfur containing analog of D-glucose
π SIMILAR VOLUMES
Acid methanolysis of 5-deoxy-5-thio-D-glucose derivatives gave the $-O-methyl glycoside 4 and the 4,6-di-0-methylated dimethyl acetal 1, indicating transannular participation of the sulfur atom. Similarly, acetolysis of the corresponding per-O-alkylated glucosides gave the 1,4diacetates, 13 and 17.
Three routes were investigated for the conversion of D-glucose into the title compound. In the first approach, reduction of the 5,6-thiirane ring of 5,6-dideoxy-5,6-epithio-1,2-O-isopropylidene-t~-D-glucofuranose (17) as well as that of its 3-O-allyl derivative (13) with lithium aluminium hydride wa