Glucitol -1 -thio

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

Phenyl l-thio-0-D-glucopyranoside tetraacetate to 1,5-anhydro-D-glucitol... 

C12HJ9CIN4O5S l-(6-Chloropurin-9-yl)-l-S-ethyl-l-thio-D-g(ycero-D-ido-hexitol [(l-S)-l-(6-chloropurin-9-yl)-l-S-ethyl-l-thio-D-glucitol] (CLPTGL10)149... 

In a different synthesis of 1,5-anhydrohexitols from a compound having a pyranoid ring, Lehmann and Friebolin31 treated 1,5-anhydro-2-deoxy-D-arafemo-hex-l-enitol (D-glucal) (20) with a-toluenethiol in the presence of light, and obtained l,5-anhydro-2-S-benzyl-2-thio-D-mannitol (21) and the epimeric anhydro-D-glucitol in equal amounts. 

Dianhydro-2,5-di-0-benzoyl-2,5-dithio-L-iditol (138), together with 1,4 3,6-dianhydro-2-5-benzoyl-5-(9-methylsulfonyl-2-thio-D-glucitol (139) was prepared203 from isomannide 2,5-dimesylate (124) (see Scheme 34). On use of a longer reaction time, compound 138 was the sole product. 

A synthesis of 4,5-dithio-L-xylose, a thio sugar in which the competition between sulfur-containing furanose and pyranose rings could be studied, has not yet been successful. Periodate scission of 3,4-0-isopropylidene-l,2-dithio-l,2-(thiocarbonyl)-D-glucitol led to an aldehyde which could not be isolated in pure form. ... 

Anhydro-4-0-(/3-D-galactopyranosyl)-D-glucitol (48) was prepared by the catalytic, reductive desulfurization of 2-naphthyl l-thio-/3-lactoside. ... 

Many known addition reactions of sulfur-containing reagents to unsaturated sugar derivatives involve free radical processes. For example, when triacetyl-D-glucal 81 is treated with thio-lacetic acid in the presence of free radical initiators, the mixture of 2-thio-D-mannitol 149 and glucitol 150 is formed (O Scheme 67) [110]. 

Radical addition to peracetylated glycals, however, yields the opposite regioselectivity and poorer stereoselectivity and 2-thio-D-glucitols and mannitols are here the normal products (O Scheme 25) [97,99,100]. 

The natural a-glucosidase inhibitor salacinol (9) (see Vol. 31, p. 163, ref. 29) and its diastereomer 10 have been synthesized by opening of the cyclic sulfates 8 and its 1,3-cyclic sulfate equivalent, respectively, with l,4-anhydro-4-thio-D-arabinitol. On treatment with NaNs in DMSO the thiepane 11, readily available from D-glucitol, underwent direct Sn2 substitution of one of the mesylate groups by azide, while the other mesylate group was diplaced transannularly by sulfur. Attack of Ns on the the resulting bicyclic sulfonium salts aiforded a 5 1 mixture of l,4-anhydro-4-thio-hexitols 12 and 13. ... 

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