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O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing O-Acyl-Protected Glycosyl Donors

✍ Scribed by Böhm, Gerd ;Waldmann, Herbert

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
496 KB
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

O‐Glycosides of pivaloyl‐protected glucose can be synthesized under neutral conditions in moderate yields by employing the pivaloylated β‐glucosyl fluoride 2d and the respective β‐benzyl phosphate 2e as glycosyl donors and 1 M solutions of LiClO~4~ in CH~2~Cl~2~ or CHCl~3~ as reaction media. The acetyl‐protected α‐ or β‐configured glucosyl trichloroacetimidates 1a and 1b were converted into the orthoesters 6 which were isolated in moderate to high yields. Under these conditions, acetyl‐protected glycosyl phosphates, acetyl‐ or pivaloyl‐protected glycosyl bromides and O‐pivaloylated glycosyl trichloroacetimidates were not converted to the desired O‐glycosides.

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O-Glycoside Synthesis under Neutral Cond
O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing Benzyl-Protected Glycosyl Donors
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## Abstract The benzyl‐protected glucosyl trichloroacetimidates, phosphates, and halides 1 are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiClO~4~ in ether, CH~2~Cl~2~, CHCl~3~, or CH~3~CN and react under these conditions with the model a

O-Glycoside Synthesis with Glycosyl Iodi
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## Abstract Glycosyl phosphates, imidates, trifluoroacetates, chlorides, and bromides are converted into the respective glycosyl iodides by treatment with LiI or NaI in 1 M solutions of LiClO~4~ in CH~2~Cl~2~. Under these neutral conditions the reactive glycosyl iodides are activated, and react wit