Alditol Anhydrides

Anhydro Sugar Formation in Acid and Base Hydrolyses of 3,4-Di-O-methylsulfonyl-D-mannitol: a Rapid Route to 1,4:3,6-Dianhydro-D-iditol(D-Isoidide)

“…The singlet for H-3 (-H4) is masked by the DOH peak. 4 In addition to the data outlined in the preceding paragraph, the relative amounts of 2a, 30, and 5a present at any stage can be readily determined by acetylating the crude mixture and studying its n.m.r. spectrum.…”

“…However, in alkaline media three-and five-membered rings appear to be favored, the smaller ring being formed more readily (2)(3)(4)6). This conclusion is upheld in the present study (Scheme 1) since base hydrolysis of 2a gave 4 but no 3a.…”

“…The crystalline products had the following physical constants. ,3: 4,4 (a) The diisopropylidene-dimesylate I n (1.0 g), was deacetonated as described above to give syrupy 2a which was dissolved in 30 cc dry methanol. Barium methoxide (0.0048 mol) in 10 cc methanolic solution was added, and after 2 h the reaction mixture was processed as described by Tipson and Cohen (12) with the exception that the product was freed from inorganic salts by extraction into isopropyl alcohol and filtration.…”

“…[Traduit par le journal] An indication of the importance of anhydro sugars is provided by the fact that a recent review volume contained three articles dealing directly with their chemistry (2)(3)(4). As a sub-group of anhydro sugars, the alditol anhydrides are prominent, not only because of what their formation reveals about intramolecular interactions and rearrangements (5,6) but also because of their increasing industrial biological importance (4,7 ) .…”

“…As a sub-group of anhydro sugars, the alditol anhydrides are prominent, not only because of what their formation reveals about intramolecular interactions and rearrangements (5,6) but also because of their increasing industrial biological importance (4,7 ) . The dianhydrohexitols, for example, have a range of clinical en~ployment that includes coronary care,' regulation of glaucoma (8) and cerebro-spinal fluid pressures (9), and emulsifiers for injectable medications 'For a preliminary account of this work, see ref.…”