Glucofuranoside ethyl 1-thio

Glucofuranoside, ethyl 1-deoxy-l-thio-a-D-, 32, 39 jS anomer, 32, 39 —, methyl o,/9-d-, 25 —, methyl 3,6-anhydro-a-n-, 39 Gluconic acid, d-, 14,15 lactones of, 11,15,20,21 —, 2-amino-2-deoxy-n-, 54 ethyl ester, 56... 

In 1916, Schneider and Sepp 1 prepared ethyl 1-thio-a-glucofuranoside by treating an aqueous solution of one mole of the diethyl dithioacetal with one mole of mercuric chloride, and maintaining neutrality by neutralizing the hydrochloric acid formed with aqueous sodium hydroxide. The product was regarded by them os a normal (i.e., pyranoid) 1-thiogly-... 

The methyl, propyl, and benzyl 1-thio-a-D-glucofuranosides were prepared" by the original method (with neutralization by sodium hydroxide). Use of the method of Pacsu and Wilson" gave the methyl, ethyl, propyl, and isopropyl 1-thio-a-D-ribofuranosides in yields ranging from 65 to 80%. Sodium (methyl l-thio-a-D-glucofuranosid)uronate and the ethyl and propyl analogs were obtained 7 similarly from the sodium salt of the... 

Pathway C has been demonstrated for both the ethyl and benzyl l-thio-a-n-glucofuranosides these compounds were converted,61 in ethanol... 

A new route, from 1-thio-D-aldohexofuranosides, was developed by Wolfrom and coworkers ethyl 1-thio-a-D-glucofuranoside was converted by chlorine into the chloride,101 arid this was condensed with the chloro-mercuri derivative of a 2,6-diacetamidopurine to give, on partial deacetylation, a 2-acetamido-9- f-D-glucofuranosyladenine.70 D-Galactofuranosyl analogs were also prepared. 

Similarly, establishment of a furanoid ring in a compound of undetermined structure was applied by Green and Pacsu82 to ethyl 1-thio-a-D-glucofuranoside the observed specific rotation of this compound in aqueous... 

It is possible to degrade 2-amino-2-deoxyhexoses to 2-amino-2-deoxy-pentoses by means of chain-shortening reactions from the nonreducing end of the molecule. Thus, Wolfrom and Anno38 converted ethyl 2-acetamido-2-deoxy-1 -thio-a-d-glucofuranoside (XV) into 2-amino-2-deoxy-a-D-xylose hydrochloride (XVI) by sequential application of periodate oxidation, borohydride reduction, and hydrolysis, as in the following reaction scheme. 

In an investigation of the hydrolysis of ethyl 1-thio-a-n-glucopyranoside, Pacsu and Wilson found that rotational change could not be used to determine the hydrolysis rate-constant, because, in addition to D-glucose, ethyl S-D-glucofuranoside and ethyl a-o-glucopyranoside are formed. 

Ethyl 2-acetamido-2-deoxy-l-thio-a-D-glucofuranoside (103) was oxidized with lead tetraacetate to the partially protected dialdose (104), which, with nitromethane, gave a mixture of the 5-epimeric 6-nitro thioglycosides (105). The 2-acetamido-2,6-dideoxy-6-nitro-hexoses (106) produced therefrom by desulfurization with mercuric chloride were not separated, but were cyclized immediately, in the presence of barium hydroxide, to a mixture of l-acetamido-l,3-di-deoxy-3-nitroinositol salts (107). Acidification, hydrogenation, and acetylation then afforded 108 (and a stereoisomer). 

Et glycoside, tetra-Ac Ethyl 2,3,5,6-tetra-O-acetyl-l-thio-a-D-glucofuranoside C,6H2409S 392.426 Mp 62-64°. 

Ethyl 2-O-acetyl-l-thio-a-L-rhamnopyranoside, T-86 Ethyl 2-O-acetyl-l-thio-p-L-rhamnopyranoside, T-86 Ethyl 2-(2-acetyl-3,5,6-tri-O-benzyl-a-D-glucofuranoside, E-28 Ethyl 2-0-acetyl-3,5,6-tri-0-benzyl-p-D-glucofuranoside, E-28 Ethyl 2-amino-2-deoxy-a-D-glucofuranoside, A-266 Ethyl 2-amino-2-deoxy-a-D-glucopyranoside, A-266 Ethyl 2,5-anhydro-a-L-arabinofuranoside, A-503 Ethyl 3,6-anhydro-7-0-benzoyl-2-deoxy-4,5-0-isopropylidene-D-fl//o-heptonate, A-532... 

Ethyl 4, 0-benzylidene-l-thio-p-D-glucopyranoside, T-70 Ethyl 4-0-benzyl-2-0-methyl-l-thio-a-D-rhamnopyranoside, T-86 Ethyl 3-0-benzyl-l-thio-a-D-arabinofuranoside, T-57 Ethyl 4-0-benzyl-l-thio-a-D-rhamnopyranoside, T-86 Ethyl 5,6-bis-0-(4-chlorobenzyl)-3-0-propyl p-D-glucofuranoside, C-140 Ethyl bis(ethylthio)acetate, G-559 Ethyl cellulose, C-48 Ethyl 6-deoxymannoside, E-27 Ethyl 6-deoxy-3-0-methyl-p-L-glucopyranoside, D-142 Ethyl 4-deoxy-p-L-crji/ira-pentopyranoside, D-347 Ethyl 2,6-diacetamido-2,3,4,6-tetradeoxy-a-D-g/ cero-hex-4-enopyranoside, D-469... 

Equimolar amounts of ethyl 1-thio-a-D-glucofuranoside and tris(diethylamino)-phosphine heated 2 hrs. at 90° in pyridine ethyl 1-thio-a-D-glucofuranoside 3,5,6-bicyclophosphite. Y 82%. E. E. Nifant ev et al., Izvest. 7975,1462 C,A,83, 193631. 

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