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Derivatives of 5-deoxy-5-mercapto-d-glucose

✍ 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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✦ 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


πŸ“œ SIMILAR VOLUMES


Sulfur participation in methanolysis and
✍ Hironobu Hashimoto; Hideya Yuasa πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 254 KB

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.

Synthesis of 6-deoxy-5-thio-d-glucose
✍ Γ‰va BozΓ³; SΓ‘ndor Boros; JΓ‘nos Kuszmann; Eszter GΓ‘cs-Baitz πŸ“‚ Article πŸ“… 1996 πŸ› Elsevier Science 🌐 English βš– 834 KB

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