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The synthesis of 1,2:5,6-di-O-isopropylidene-d-mannitol: a comparative study

✍ Scribed by János Kuszmann; Éva Tomori; Ingrid Meerwald

Publisher
Elsevier Science
Year
1984
Tongue
English
Weight
775 KB
Volume
128
Category
Article
ISSN
0008-6215

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✦ Synopsis

Three different methods of acetonation of D-mannitol using (a) acetone and zinc chloride, (6), 2,2_dimethoxypropane, l,Zdimethoxyethane, and tin(I1) chloride, and (c) 2-methoxypropene, N, N-dimethylformamide, and p-toluenesulfonic acid were studied in detail and compared, using gas-liquid chromatographic techniques. In each reaction, isomeric diacetals are formed, but method a gives the 1,2:5,6_diacetal in the highest yield (63%). Methods b and c give a more complex mixture of acetals than proposed in the literature, and both methods are less economical than n. A new 1,2:3,6:4,5-tri-O-isopropylidene-D-mannitol could be separated, and its graded hydrolysis was compared to that of the 1,2:3,4:5,6-D-iacetal.

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