5-Thio-D-glucopyranose

The synthesis of a bridgehead sulfonium salt analogue 59, of the naturally occurring glycosidase inhibitor castanospermine, proceeded by a multistep procedure starting from 5-thio-d-glucopyranose pentaacetate <2000JA10769>. The desired bicyclic sulfonium salt 57 could not be obtained from the key bromide precursor... 

Adley and Owen [3] described the synthesis of 5-thio-L-idopyranose 12 by the ring opening of 5,6-dideoxy-5,6-epithio-l,2-0-isopropyhdene-a-L-idofuranose 13, with potassium acetate in a mixture of glacial acetic acid and acetic anhydride and subsequent deprotection. 5-Thio-D-glucopyranose 10 was first synthesized by Feather and Whistler [8]. 

Hoffman, D J, Whistler, R L, Diabetogenic action of 5-thio-D-glucopyranose in rats. Biochemistry, 1, 4479-4483, 1968. 

Whistler, R L, Lake, W C, Inhibition of cellular transport processes by 5-thio-D-glucopyranose,... 

Nakamura, M, Hall, P F, Inhibition by 5-thio-D-glucopyranose of protein biosynthesis in vitro in spermatids from rat testis, Biochim. Biophys. Acta, 447, 474-483, 1976. 

Pitts, M J, Chemielewski, M, Chen, M S, Abd El-Rahman, M M A, Whistler, R L, Metabolism of 5-thio-D-glucopyranose and 6-thio-D-fructopyranose in rats. Arch. Biochem. Biophys., 169, 384-391, 1975. 

Hasegawa, A, Kawai, Y, Kasugai, H, Kiso, M, Synthesis of 2-acetamido-2-deoxy-5-thio-D-glucopyranose, Carbohydr. Res., 63, 131-137, 1978. 

Guthrie, R D, O Shea, K, The s3mthesis of 2-acetamido-2-deoxy-5-thio-D-glucopyranose and its derivatives, Aust J. Chem., 34, 2225-2230, 1981. 

Bognar, R, Herczegh, P, Whistler, R L, Madumelu, E B, 2-Acetamido-2-deoxy-5-thio-D--glucopyranose (5-thio-A-acetyl-D-glucosamine), Carbohydr. Res., 90, 138-143, 1981. 

Thio-D-xylopyranose (4) was prepared by the same group and also by Schwarz and Yule [5] as well as by Whistler and co-workers [9,10]. 5-Thio-D-glucopyranose (5) was first synthesized by Feather and Whistler [11],... 

A synthesis of 6-amino-6-deoxy-5-thio-D-glucopyranose. in wliich the key step was the stereospecific addition of BnSH to the alkene 3-O-acetyl-5,6-dideoxy-l,2-0-isopropylidene-6-nitro-a-D-xv/o-hex-5-enofuranose, was described. Methyl... 

Under similar reaction conditions, treatment of the thio sugar 1,2,3,4,6-penta-O-acetyl-5-thio-D-glucopyranose was shown to give the 1,2-trans azide 66, accompanied by minor amounts of the l,2-c product. Another approach to 66 employs the a-bromide 67 and LiNs. A protecting group at C-2, less prone to form an acetoxonium ion (compare 54), results in the loss of stereoselectivity. ... 

Tetra-Ac 1,2,3,4-Tetra-0-acetyl-6-deoxy-5-thio-D-glucopyranose [185802-54-4]... 

Tetra-0-acetyl-6-deoxy-5-thio-D-glucopyranose, D-373 Tetra- O -acetyl-1 -deoxy-D-xylitol, D-385 T,2,4,4 -Tetra-0-acetyl-3,6 3, 6 -dianhydrosucrose, A-699... 

Thio-D-glucose has been demonstrated to be a substrate for lactose synthetase which converts it into 5-thio-lactose. The reaction of r/c-epoxides with thiourea to yield y/c-epithio-compounds has been used to synthesize 2-acetamido-2-deoxy-5-thio-D-glucopyranose as portrayed in Scheme 5. Two further papers on the reaction of epimines with sulphur-containing compounds have appeared (see Vol. 11, p. 97). Reactions leading to... 

Based on a wide range of crystallographic data of the mutant enzymes with D-xylose (18),5-thio-D-glucopyranose (38) or 5-deoxy-D-xylulose (39) (Scheme 15) in their active sites, this view was not supported by the investigators. An in-... 

Acetamido-2-deoxy-5-thio-D-glucopyranose (7), and -D-manno-pyranose (8), have been synthesized as shown in Schemes 2 and 3 ... 

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