ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Triphenylmethyl derivatives of L-sorbose
Research Institute of Food Industry, Bratislava
Abstract: CPh3Cl gives readily hydrolyzable ethers with primary OH groups. The reagent is used for sepn. of mixtures of structurally isomeric L-sorbose derivs. CPh3Cl is added to Me L-sorboside in C5H5N at 0°, the soln. filtered after 48 hrs. at room temp., Ac2O added to the filtrate, which is kept 24 hrs. at 0° and 24 hrs. at room temp., and finally poured on ice, giving 1-trityl-α-methyl-L-sorboside 3,4,5-triacetate, C32H34O9 (I), m. 185°, [α]57820 76.85° (C6H6), 56.2° (CHCl3). I in AcOH-HBr gives α-Me L-sorbopyranoside 3,4,5-triacetate, C13H20O9, m. 81°, [α]57820 -70.9° (C6H6), -56.25° (MeOH). 1,6-Ditrityl-2,3-isopropylidene-L-sorbofuranose 4-acetate in AcOH and HBr afford 2,3-isopropylidene-L-sorbofuranose 4-acetate, C11H18O7, m. 100°, [α]57820 0° (H2O), 23.0° (CHCl3). 2,3:4,6-Diisopropylidene-L-sorbofuranose and CPh3Cl in C5H5N give the 1-trityl deriv., m. 182°, [α]57820 -29.6° (CHCl3). The mixt. of 1,2-isopropylidene-L-sorbopyranose (II) and 2,3-isopropylidene-L-sorbofuranose (III) obtained by acetonation of L-sorbose can be sepd. by tritylation, giving a ppt. of the 1,6-ditrityl deriv. from III, while II can be recovered from the filtrate.
Full paper in Portable Document Format: 11a2.pdf (in Slovak)
Chemical Papers 1 (1) 2–15 (1947)