5-Thio-D-galactose

Alkoxythiatetrahydropyrans were also studied (58, 59). It was found that the major isomer (90%) had the axial conformation 61 rather than the equatorial conformation 62 when R is a methyl or a propyl group. Also, Perlin and Nam Shin (60) have carried out the methanolysis of 5-thio-D-galactose... 

Most of the other important 5-thiopyranoses such as 5-thio-D-mannose (32) [55], 5-thio-D-galactose (33) [56], and 5-thio-D-allose [57] have been synthesized. 

A sulfur-containing, septanose form is only obtainable as a result of the protection of the C-5 and C-4 hydroxyl groups in such a way that the pyranose or furanose rings cannot be formed. 2,3,4,5-Tetra-O-acetyl-S-acetyl-6-thio-D-galactose diethyl dithioacetal (273), obtained from the corresponding 6-p-toluenesulfonate with potassium thioacet-ate, undergoes hydrolysis in the presence of mercuric chloride and... 

Bushway, A, Keenan, T W, 5-Thio-D-glucose is an acceptor for UDP-galactose D-glucose 1-galactosyltransferase, Biochem. Biophys. Res. Commun., 81, 305-309, 1978. 

Raney nickel in aqueous ethanol normally acts to substitute hydrogen atoms in place of all of the alkyl-(or aryl- or other)thio groups present in a dithioacetal, without disturbing other substituents thus, the 2-S-ethyl-2-thio-D-pentose diethyl dithioacetal137 156, 5-S-ethyl-5-thio-D-arabinose diethyl dithioacetal145 (157), and 2,3,4,5-tetra-0-acetyl-6-S-acetyl-6-thio-D-galactose diethyl dithioacetal or its 6-thiocyanato analogue346 (158) react with Raney nickel to... 

Thio-D-maimose 329,5-tliio-D-galactose 330,5-thio-L-altrose 331, and 5-thio-L-fucose 332" were synthesized using as the key steps the conversion of a terminal oxirane into thiirane with thiourea, and the opening of the thiirane... 

The following are not substrates D>allose, D-galactose 4-deoxy-glucose, 4>deoxy-fluoroglucose, 5-thio-D glucose, L-rhamnose, L-fucose, L-sorbose. 

Cox and Owen [42] and Whistler and Campbell [43] provided early synthetic approaches to the 6-thioseptanose system. The latter workers prepared a protected open-chain 6-thio dithioacetal of D-galactose that, upon deprotection at C-1 and S-6, could be cychzed to form the corresponding l,2,3,4,5-penta-0-acetyl-D-galacto-6-thioseptanose 37. From this intermediate, several derivatives, such as both anomers of the thioseptanosyl chloride as well as the methyl thioseptanosides, were synthesized. The methyl thioseptanoside was found to be more prone to hydrolysis than the corresponding sulfur containing pyranoid glycoside. 

Glycosylation of 1,2 3,4-di-O-isopropylidene-D-galactose (412) with tri-0-acct l-5-thio-L-arabinopyranosyl bromide (411) in the presence of silver triflate and tetramethylurea gave the 5-lhiodisacharide 413, Compound 411 was obtained from acetylated 5-G-losyl-L-arabinose dibenzyl dithioacetal by cyclization with sodium iodide-barium carbonate in butanone (82%) followed by bromination with Br in CCI4 (76%).2 2... 

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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