- Highly stereoselective synthesis of the 1-O-acylglycosyl ester of diclofenac via glycosyl phosphorothioates, -selenoates and -dithioates as glycosyl donors
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Stereoselective glycosylation of o-(2,6-dichloroanilino)phenylacetic acid (Diclofenac, 1), as a free carboxylic acid with glycosylthio (2a-c), -dithio (3a-e) and -selenophosphates (4a-c) as glycosyl donors is reported. The reactions were carried out in ap
- Borowiecka, Joanna
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- Convenient synthesis of S- and Se-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-phosphorothioate, phosphoroselenoate and phosphorodithioate
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Organic phosphorothioate 7, phosphoroselenoate 8 and phosphorodithioate 9 were glucosylated with 2,3,4,6-tetra-O-benzyl-D-glucopyranose derivatives 1-6. When the reaction was performed in the presence of boron trifluoride etherate, the products were 5-α-glucosyl and Se-α-glucosyl phosphoroethers 10-12. O-Benzylated glucosyl halides 5-6 with alkylammonium salt of 9 afforded S-β-glucosyl phosphorodithioate 13, which underwent the β?α anomerization by boron trifluoride etherate into more stable α-derivatives.
- Kudelska
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p. 1548 - 1552
(2007/10/03)
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