A.
6-Trityl-β-d-glucose-1,2,3,4-tetraacetate. A mixture containing
120 g. (0.67 mole) of anhydrous glucose,
193.2 g. (0.7 mole) of trityl chloride, and
500 ml. of anhydrous pyridine [Org. Syntheses Coll. Vol. 1, 100 (1941)], is heated on the steam cone until solution is complete (Note
1). Without cooling,
360 ml. of acetic anhydride is added in one portion (Note
2). After standing for 12 hours, the reaction mixture is poured slowly into 10 l. of ice water, to which
500 ml. of acetic acid has been added, and the resulting mixture is vigorously stirred mechanically for 2 hours (Note
3). The precipitate is filtered and is immediately stirred for a short time with 10 l. of ice water. The white, granular precipitate is filtered, washed well with cold water, and then air-dried (Note
4). The dried solid is digested with
500 ml. of ether (Note
5). The insoluble portion is dissolved in hot
95% ethanol (approximately 3 l.), and the solution is decolorized and filtered while hot. The filtrate, upon cooling, deposits fine needles of
6-trityl-β-d-glucose-1,2,3,4-tetraacetate of sufficient purity for further use. The yield at this point is about
169 g. (
43%). Recrystallization from
95% ethanol gives the pure compound which melts at
166–166.5°. In
pyridine,
[α]19D is + 44.8°;
[α]28D, +45.3°. The yield of purified material is
137 g. (
35%) (Note
6).