1,6-anhydro 6-thio

The preparation of a number of anhydro thio sugars is based on this S neighboring-group participation. 

Four-membered anhydro thio sugars have also been prepared by reactions that involve neighboring S groups. The D-mannitol derivative (282) was converted into the tricyclic D-iditol derivative (283) with methanolic... 

A total synthesis of erythromycin A involved use of the thiogly-coside of the anhydro-thio sugar (12) which allowed easy glycosyl-... 

Inosine, 6-benzyloxy-9- -D-ribofuranosyl-2-dimethylamino-hydrogenolysis, 5, 558 Inosine, 2 -deoxy-alkylation, 5, 538 Inosine, 6-phenacylthio-dethiation, S, 559 Inosine 5 -monophosphate biosynthesis, 1, 88 Inosines, thio-synthesis, 5, 584 Inositol, D-l,4-anhydro-synthesis, 1, 416 Inositols synthesis, 1, 416 Insecticides... 

Spiro systems can be named by normal procedures [13]. For clarity, any anhydro or deoxy prefixes or chalcogen replacement prefixes (e.g. thio) referring to the spiro... 

Anhydro-a-D-fructofuranose P-D-fructopyranose l,2 2,l -dianhydride (55) 6-Deoxy-6-isothiocyanato-a-D-fructofuranose P-D-fructopyranose 1,2 2,1 -dianhydride (56) 6-Deoxy-6-iodo-a-D-fructofuranose 6-deoxy-6-iodo-p-D-fructofuranose 1,2 2,1 -dianhydride (57) 6-Chloro-6-deoxy-a-D-fructofuTanose 6-chloro-6-deoxy-P-D-fructofuranose 1,2 2,1 -dianhydride (58) 6-S-Heptyl-6-thio-a-D-fruclofuranose 6-S-heptyl-6-thio-p-D-fructofuranose 1,2 2,1 -dianhydride (59) 6-Azido-6-deoxy-a-D-fructofuranose 6-azido-6-deoxy-P-D-fructofuranose 1,2 2,l -dianhydride (60) 6-Amino-6-deoxy-a-D-fructofuranose 6-amino-6-deoxy-p-D-fructofuranose 1,2 2,1 -dianhydride (61) 6-Acetamido-6-deoxy-[Pg.260]

CgHioC S 1,6-Anhydro-1 (6)-thio-/ -D-glucopyranose [ 1 (6)-thiolevo- TLEVGL 38 423... 

A hydroxysulfoxide was desulfurized with Ra-Ni in MeOH for 30 minutes.400 Treatment with hydrogen in the presence of catalytic amounts of Ra-Ni in EtOH caused the desulfurization of a 2,6-anhydro-2-thio sugar, the reduction of an N-oxide, and the removal of benzyl and carbomethoxy groups at the... 

Shortly after the above work appeared, Bolliger and Prins90 reported a similar synthesis leading to a 3- rather than a 2-desoxy derivative. Methyl 2,3-anhydro-4,6-benzylidene-a-D-mannoside (LXIV), upon treatment with sodium thiomethoxide, was converted into methyl 3-methyl-thio-4,6-benzylidene-a-D-altroside (LXV) which, after desulfurization and rebenzylidenation, gave methyl 3-desoxy-4,6-benzylidene-a-D-man-noside (LXVI). Methylation of LXV with methyl iodide and silver oxide followed by desulfurization gave methyl 2-methyl-3-desoxy-4,6-benzylidene-a-D-mannoside in poor yield. 

Tetraacetyl-l-thio-/S-D-glucose to tetraacetyl-l,5-anhydro-i>-glueitol 2.4 U (t tl <4 — 17... 

Phenyl 1 -thio-a-D-arabinopyranoside triacetate to 1,5-anhydro-D-arabitol... 

Phenyl l-thio-/S-cellobioside heptaacetate to 1,5-anhydro-4- (d-D-gluco-pyranosyl)-D-glucitol heptaacetate... 

Naphthyl l-thio-/J-D-galactopyranoside tetraacetate to 1,5-anhydro-D-galactitol tetraacetate... 

Notiz iiber l,6-Anhydro-2-S-benzyl-2-thio-/3-l>idopyranose, by L. Vegh and E. Hardegger, Helv. Chim. Acta, 56 (1973) 1961-1962. 

C6H10O4S 1,6-Anhydro-l(6)-thio-/3-D-glucopyranose l(6)-thiolevo-glucosan (TLEVGL)19... 

Verbindungen, die S im 1,6-Anhydro-Ring enthalten, sind gleichfalls darstellbar 2,266), Aus der 6-0-p-Toluolsulfonyl-l-desoxy-l-acetylthio-2,3,4-tri-0-acetyl-p-D-glucop5u anose wurde durch die Einwirkung von CHsONa l,6-Anhydro-6-thio-p-D-glucop3u anose erhalten ... 

Under acidic conditions, benzylated l,6-anhydro-/J-D-glucose (1) was also used as a donor with 4-thio-glucose (2 a) or 4 -thiomaltose derivatives (2 b) and the condensation afforded a-linked thio-di (3 a) or trisaccharides (3 b) in fair yields [6] (Scheme 1). It is noteworthy that 1,6-anhydro-di- and trisaccharide are unreactive under these conditions. 

Reaction of benzyl a-D-glucopyranosyl cyclic sulfate 44 or benzyl a-D-galactopyranosyl cyclic sulfate 45 with 1,4-anhydro-2,3,5-tri-0-benzyl-4-thio-D-arabinol 46, followed by debenzylation and reduction, gave novel sulfonium sulfate derivatives 47a and 47b, respectively, which were used to prepare homologs of salacinol 48, a natural human maltase glucoamylase inhibitor, as lead candidates for the treatment of type 2 diabetes (Scheme 3) <2006JOC1111>. 

C-3 in the unsubstituted compound.176,177 However, at the time of these experiments, only C-3 substitution had been observed with 2,3-anhydropentofuranosides, and the results of investigation of this reaction suggest that the amino sugar substituted at C-2 is the major product.184 With thiocyanate ion, substitution also occurs at C-3, leading to the thietane derivative, namely, methyl 3,5-anhydro-3-thio-a-D-xylofuranoside (59) but, as this compound was obtained in only 25% yield, the major pathway may involve 2-substitution, leading to products not characterized.178... 

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