Glucitol 5-nitrate, 1,4.3,6-dianhydro-2-0-

The crystal and molecular structures of l,4 3,6-dianhydro-2-0-(p-bromophenylsulfonyl)-(exo)-D-glucitol 5-nitrate(endo) were reported by Camerman, Camerman, and Trotter.69 The bond distances and valency angles were found to be normal, with an intramolecular apparent attraction between an oxygen atom of the N02 and the ring-oxygen atom of the second ring the distance was found to be 0.29 nm. 

Four X-ray investigations of isohexide derivatives have been published.39-42 The oldest of them gave very little information about structural details. Two crystallographically independent molecules of 1,4 3,6-dianhydro-2-0-(p-bromophenylsulfonyl)-D-glucitol 5-nitrate (30), having the same conformation, are in the asymmetric unit. 

Ci2Hi2BrNUgS l,4 3,6-Dianhydro-2-0-(p-bromophenylsulfonyl)-D-glucitol 5-nitrate BSGLON 31 367... 

The synthesis of l,4 3,6-dianhydro-D-glucitol 5-nitrate from the 2,5-dinitrate is covered in Chapter 18. 

With a cold mixture of nitric and sulfuric acids, styracitol gives a crystalline, explosive tetranitrate 99). With the same reagent, 1,4 3,6-dianhydro-D-glucitol and 1,4 3,6-dianhydro-D-mannitol give crystalline dinitrates, whereas 1,4-anhydro-D-glucitol and 1,4-anhydro-D-mannitol yield sirupy products. These anhydride nitrates show depressor action, similar to that of glycerol trinitrate and D-mannitol hexanitrate 100). 

D-Glucitol is converted to a mixture of 1,4-anhydro-D-glucitol, 2,5-anhydro-L-iditol, 2,5-anhydro-D-mannitol and l,4 3,6-dianhydro-D-glucitol on treatment with hydrogen in the presence of a Cu-Ru catalyst. Reactions of other alditols with bimetallic catalysts are described. The preparations of three stereoisomers (exo, endo endo, exo endo, endo) of the known Chem. Abstr., 1991, 115, 136 644) dianhydro nitrate derivative 27 (exo, exo form) have been reported and the enzymatic preparations of l,4 3,6-dianhydro-D-glucitol mono acetates is mentioned in Chapter 7. 

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