This is another example of the greater tendency of secondary, compared to primary, hydroxyl groups to participate in the formation of cyclic acetals. Intramolecular Hemiacetal formation is common in sugar chemistry. Molecules which have an alcohol and a carbonyl can undergo an intramolecular reaction to form a cyclic hemiacetal. For Part III, see ref. ***The formula shows the L isomer. We use cookies to help provide and enhance our service and tailor content and ads. Copyright © 1978 Published by Elsevier Ltd. https://doi.org/10.1016/S0008-6215(00)84314-1. 230 INTRAMOLECULAR ACETAL FORMATION acetate gave a spectrum in which every signal could be assigned; the spectrum of the anhydride itself could be interpreted by comparing it with the spectrum14 of 1,6- anhydro-O-D-mannopyranose (2). 1. For example, the common sugar glucose exists in the cylcic manner more than 99% of the time in a mixture of aqueous solution. On acid-catalyzed equilibration in aqueous solution, three aldoheptoses, d-glycero-l-manno-, d-glycero-l-allo-, and d-glycero-l-altro-heptose, give 15, 54, and 98%, respectively, of the 1,6-anhydropyranose, a much higher proportion than is formed from the homomorphous aldohexoses. By continuing you agree to the use of cookies. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Intramolecular acetal formation by primary. Conformational Analysis in Carbohydrate Chemistry: Part IV. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Formation of Cyclic Hemiacetal and Acetals.
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