Thio-D-glucoside

The lower rates of hydrolysis (see Table IX) found for 1-thio-D-gluco-furanosides are attributable to the lower basicity of the sulfur atom,141 and thus, less protonation of the 1-thio-D-glucoside occurs in acid solution, in comparison to the D-glucofuranosides. 

Many aryl- and also thio- -D-glucosides produce yellow fluorescent ehromato- ... 

In this Section, the naturally occurring 1-thio-D-glucosides are discussed first. Chemically synthesized 1-thioglycosides and their reactions are then considered. Other iS-substituted derivatives of the 1-thio sugars, which normally react by cleavage of the /S-substituent to give the free 1-thio-aldoses, are treated in Section III (p. 152). 

Thio- -D-glucoside l-[3-methyl-N-(sulfooxy)butanimidate], 9CI. Isobutyl glucosinolate [38226-91-4]... 

Dutton, G.J. and tiling, H.P.A. (1972) Mechanism of biosynthesis of thio-p-D-glucuronides and thio-p-D-glucosides. 

Mercaptolysis of /3-D-glucopyranose pentaacetate in ethyl mercaptan at 0°, with zinc chloride as catalyst, gives ethyl tetra-O-acetyl-l-deoxy-1-thio-/S-D-glucopyranoside in 71% yield. Under the same conditions, a-D-glucopyranose pentaacetate reacted only very slowly, but it could be shown that the deoxy-thio-/3-D-glucoside is formed in much greater amount than is the a anomer. Mercaptolysis of the D-mannopyranose pentaacetates under the same conditions for 48 hours resulted in a 70% yield of ethyl tetra-O-acetyl-l-deoxy-l-thio-a-D-mannopyranoside from the /3-D-pentaacetate, and in a 60% yield from the a anomer.103 Inspection, by preparative paper chromatography, of the residual sirups, after deacetylation, led in each case to the isolation of the anomeric ethyl-1-... 

Attempts to purify the potato lectin on ovomucoid- and N,N -diacetylchitobiose-substituted Sepharose failed the lectin was so strongly bound that it could not be removed from the adsorbent by displacement with urea.483 To circumvent this difficulty, Delmotte and coworkers483 employed p-aminobenzyl 2-acetamido-2-deoxy-l-thio-/3-D-glucoside-substituted Sepharose, and eluted the lectin with 0.1 M acetic acid (yield 58 mg from 128 g of the protein in potato-tuber extract). 

Methanolic hydrogen chloride at elevated temperatures causes the conversion of 1,6-anhydrohexopyranoses into mixtures of the corresponding methyl glycosides.86,188,282,442 Ethyl 2,3,4-tri-O-benzyl-l-thio-a-D-glucoside was similarly obtained on treatment of 24 with ethane-thiol and zinc chloride.516,517 The anhydro bridge of levoglucosan (6)... 

The rapid formation of one mole of formaldehyde when one mole of the ethyl 1-thio-a-D-glucoside of Schneider and Sepp is oxidized with a 5-molar excess of periodate provided evidence for the furanoid ring in this compound, and the 2-molar uptake of oxidant indicated cleavage between C-5 and C-6, and, probably, between C-2 and C-3. Further oxidation, presumably at the sulfur atom, occurred on oxidation for longer than one hour. Similar results were observed with ethyl 1-thio-a-D-galactofuranoside and with ethyl 1-thioglycosides of 2-acetamido-2-deoxy-D-galactose. ... 

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