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Cyclic acetals are very much more stable against acid hydrolysis than acyclic acetals. Consequently acyclic acetals are used practically only when a very mild cleavage is required or when two different protected carbonyl groups must be differentiated in their liberation.
These protecting groups “lock” the sugars into a rigid chair conformation. When the sugar forms the necessary oxocarbenium ion, it flattens at the anomeric position. This change in configuration is a high-energy transformation when cyclic protecting groups are present, and leads to the sugar being “disarmed”. [3]
For deprotection (regeneration of the alcohol) Aqueous base (pH >9) [6]; Aqueous acid (pH <2), may have to be heated [7]; Anhydrous base such as sodium methoxide in methanol. Very useful when a methyl ester of a carboxylic acid is also present in the molecule, as it will not hydrolyze it like an aqueous base would.
However, in order for anomers to exist, the sugar must be in its cyclic form, since in open-chain form, the anomeric carbon atom is planar and thus achiral. More formally stated, then, an anomer is an epimer at the hemiacetal/hemiketal carbon atom in a cyclic saccharide. [1] Anomerization is the process of conversion of one anomer to the other.
In organic chemistry, an acetonide is the functional group composed of the cyclic ketal of a diol with acetone. The more systematic name for this structure is an isopropylidene ketal. Acetonide is a common protecting group for 1,2- and 1,3-diols. [1] The protecting group can be removed by hydrolysis of the ketal using dilute aqueous acid.
The reason for glucose having the most stable cyclic form of all the aldohexoses is that its hydroxy groups (with the exception of the hydroxy group on the anomeric carbon of d-glucose) are in the equatorial position. Presumably, glucose is the most abundant natural monosaccharide because it is less glycated with proteins than other ...
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Generic structure of acetals. In organic chemistry, an acetal is a functional group with the connectivity R 2 C(OR') 2. Here, the R groups can be organic fragments (a carbon atom, with arbitrary other atoms attached to that) or hydrogen, while the R' groups must be organic fragments not hydrogen. The two R' groups can be equivalent to each ...