51385-38-7Relevant academic research and scientific papers
En Route to Thromboxane Compounds from Carbohydrates, I. Synthesis of the Unsaturated Sugar Precursors
Pelyvas, Istvan,Lindhorst, Thisbe,Thiem, Joachim
, p. 761 - 769 (2007/10/02)
Allyl 4-C-hex-2-enopyranosides 18a-c, representing chiral precursors for the carbohydrate-based construction of the ring systems of thromboxane A2 and B2 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-glucopyranoside (9) by modification of known procedures, including selective O-benzoylation with 1-(benzoyloxy)-1H-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 reduce d stability of the 6-O-(tert-butyldiphenylsilyl) ether group under the Tipson-Cohen reaction conditions.
