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Isolierung und NMR‐spektroskopische Untersuchungen von (−)‐1‐ O ‐Benzyl‐β‐ D ‐primverosid aus grünen Früchten von Prunus laurocerasus
Author(s) -
Weinges Klaus,
Schick Hartmut,
Lautenschläger Michael,
Schilling Gerhard
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101124
Subject(s) - chemistry , hydrogenolysis , saponification , nuclear magnetic resonance spectroscopy , stereochemistry , nuclear chemistry , chromatography , organic chemistry , catalysis
Isolation and NMR‐Spectroscopic Investigations of (−)‐1‐ O ‐Benzyl‐β‐ D ‐primveroside from Green Fruits of Prunus laurocerasus The TLC of the acetylated aqueous extracts of the green fruits of Prunus laurocerasus reveals two spots corresponding to pentaacetyl‐glucopyranose and hexaacetyl‐1‐ O ‐benzyl‐β‐ D ‐primveroside ( 2 ), which can be quantitatively separated by flash chromatography. Saponification of 2 yields the free 1‐ O ‐benzyl‐β‐ D ‐primveroside ( 1 ) which affords D ‐primverose ( 3 ) upon hydrogenolysis. The direct hydrogenolysis of 2 yields hexaacetyl‐β‐ D ‐primverose ( 4 ). The structures of compounds 1–4 have been verified by NMR spectroscopy.