Mannitol dibenzoate

Brigl and Griiner45 reported the isolation of three products when 1,6-di-O-benzoyl-D-mannitol (29) was heated in boiling 1,1,2,2-tet-rachloroethane in the presence of p-toluenesulfonic acid as the catalyst. These compounds were assigned mono- and di-anhydro structures, and were later shown by Hockett and coworkers46,47 to be 1,4-anhydro-D-mannitol dibenzoate (30), l,4 3,6-dianhydro-D-man-nitol dibenzoate (31), and 2,5-anhydro-l,6-di-0-benzoyl-D-glucitol (32). The latter compound, which can be readily isolated from the... 

Preparation 214.—Mannitol Dibenzoate [1 6-Dibenzoic ester ofhexol-... 

Brigl and Grtiner reported another dibenzoyl-anhydro-D-mannitol (from the above-described reaction) which was shown (23) to be 1,4-anhy-dro-D-mannitol 2,6(or 3,6)-dibenzoate. Saponification yielded a crystalline anhydro-D-mannitol (n-mannitan) which was identical with that described previously by Valentin. The 1,4-anhydro-D-mannitol structure was established by the method of synthesis employed by Valentin ... 

In some related work, Foster and coworkers treated the di-O-iso-propylidene-D-mannitol di-p-toluenesulfonate (43) with sodium benzoate in W,W-dimethylformamide, and obtained, among a number of other products, the di-O-isopropylidene-D-iditol monobenzoate (46) and the di-O-isopropylidene-D-talitol dibenzoate (47). A rational sequence for these two products involves first, the Sn2 displacement on (43) to give the D-talitol compound (44), that yields the orthoester ion (45) by benzoyl-group participation. Conventional attack by water at C-1 leads to (46), whereas attack by benzoate ion at C-3 leads to (47). The authors suggested that participation reactions leading to (46) and (47) were... 

Mannitol dimetaborate 105), according to its analysis, appears to be an addition compound of two moles of metaboric acid and one mole of mannitol. However, on benzoylation only mannitol 1,6-dibenzoate is obtained ... 

---