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2004
Carbohydrates
U 0500
Polymer-Bound Diphenylphosphane Hydrobromide, a Mild Acid for the Activaof Enol Ethers: Applications in Polymer-Assisted Glycosidations. — Poly47- 179 tion
mer-bound diphenylphosphane hydrobromide represents an efficient but mild activating agent for enol ethers and can, thus, be used for the protection/deprotection of alcohols as tetrahydropyranyl ethers [cf. (I)/(III)]. It is shown that the novel reagent possesses an improved chemoselectivity in the deprotection of compound (IV) as compared to the analogous non-supported PPh3·HBr. A further interesting field of application is the activation of glycals for the glycosylation reaction with alcohols. This is
demonstrated especially for structurally complex alcohols. The method avoids the formation of Ferrier rearrangement products and tolerates acid-labile groups. —
(JAUNZEMS, J.; KASHIN, D.; SCHOENBERGER, A.; KIRSCHNING*, A.; Eur. J.
Org. Chem. 2004, 16, 3435-3446; Inst. Org. Chem., Univ. Hannover,
D-30167 Hannover, Germany; Eng.) — Mischke
2004
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