Preparation of Kingiside from Aucubin

Weinges, Klaus; Schick, Hartmut; Ziegler, H. J.

doi:10.1002/(sici)1099-0690(200004)2000:8<1623::aid-ejoc1623>3.0.co;2-y

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Zemplén Deacetylation

2010

Comprehensive Organic Name Reactions and Reagents

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The efficient removal of the O ‐acetyl protecting groups of carbohydrates by treatment of the O ‐acetylated substrates in methanol with a catalytic amount of sodium methoxide at room temperature is generally known as the Zemplén deacetylation, Zemplén de‐ O ‐acetylation, or Zemplen deacetylation. In addition, after the reaction, the O ‐acetyl‐protected carbohydrates are transformed into unprotected ones, in a manner analogous to the hydrolysis of an ester, thus this reaction is termed as the Zemplen saponification as well. However, it has been reported that the Zemplén deacetylation is probably not suitable for the deprotection of carbohydrates with disulfide linkages. This reaction has wide applications in carbohydrate chemistry.

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