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In carbohydrate chemistry carbohydrate acetalisation is an organic reaction and a very effective means of providing a protecting group. The example below depicts the acetalisation reaction of D-ribose 1. With acetone or 2,2-dimethoxypropane as the acetalisation reagent the reaction is under thermodynamic reaction control and results in the ...
These proceeded through 8 different protecting groups (a methyl ester, five acetals, 20 TBDMS esters, nine p‑methoxybenzyl ethers, four benzoates, a methyl hemiacetal, an acetone acetal and an SEM ester). [109] Palytoxin. The introduction or modification of a protecting group occasionally influences the reactivity of the whole molecule.
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.
Acetals, as already pointed out, are stable tetrahedral intermediates so they can be used as protective groups in organic synthesis. Acetals are stable under basic conditions, so they can be used to protect ketones from a base. The acetal group is hydrolyzed under acidic conditions. An example with a dioxolane protecting group is given below.
Cyclic acetals (8 C) Pages in category "Protecting groups" The following 19 pages are in this category, out of 19 total. This list may not reflect recent changes. ...
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] These groups can be ...
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Structure of the benzylidene acetal of glucose. In organic chemistry , a benzylidene acetal is the functional group with the structural formula C 6 H 5 CH(OR) 2 (R = alkyl, aryl). Benzylidene acetals are used as protecting groups in glycochemistry.