ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Triphenylmethyl derivatives of L-sorbose

F. Valentin

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)