Premium
En route to thromboxane compounds from carbohydrates, I. Synthesis of the unsaturated sugar precursors
Author(s) -
Pelyvás István,
Lindhorst Thisbe,
Thiem Joachim
Publication year - 1990
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.1990199001143
Subject(s) - chemistry , sulfonyl , ether , carbohydrate , sugar , ring (chemistry) , benzotriazole , anomer , carbohydrate chemistry , medicinal chemistry , organic chemistry , stereochemistry , alkyl
Allyl 4‐ C ‐[(carboxamido)‐ and (ethoxycarbonyl)methyl]hex‐2‐enopyranosides 18a – c , representing chiral precursors for the carbohydrate‐based construction of the ring systems of thromboxane A 2 and B 2 were prepared by means of the Claisen‐type rearrangement of the suitably substituted hex‐3‐enopyranosides 7a, b . The latter sugars were synthesized from allyl α‐D‐glucopyraoside ( 9 ) by modification of known procedures, including selective O ‐benzoylation with 1‐(benzoyloxy)‐1 H ‐benzotriazole ( 11 ), and Tipson‐Cohen sulfonyl ester elimination of the 3,4‐di‐ O ‐mesylates 16 and 17 . Studies on the corresponding methyl glycosides 8a – c showed a reduced stability of the 6‐ O ‐( tert ‐butyldiphenylsilyl) ether group under the Tipson‐Cohen reaction conditions.