Acetal-type protecting group

Other acetal-type protecting groups (tetrahydrofurfuryl ethers, methoxymethyl ethers, 1,3-dioxolanes) are also considered to be incompatible with oxidising agents. 

T. Mukaiyama, M. Ohshima, and M. Murakami, 2-Benzyloxy-propene A novel protective reagent of hydroxyl groups, Chem Lett 265 (1984) T. Mukaiyama, M. Ohshima, H. Nagaoka, and M. Murakami, A novel acid-resistant acetal-type protective group for alcohols, Chem. Lett 615 (1984). 

The solvent dependence of the rate of solvolysis of TBS ethers has useful implications for selective deprotection of acetal-type protecting groups. Thus, dilute... 

MOM ethers are the first and simplest of the acetal-type protecting groups whose prime virtues are ease of introduction, MOM ethers are the most robust of the alkoxymethyl ethers. In some cases, the conditions required to liberate a... 

Acetalation Reactions Acetal-Type Protecting Groups. 121... 

A review of protection at the 2 position in oligoribonucleo-tide synthesis includes discussion of a number of acetal-type protecting groups, the lability of which has been carefully tailored... 

Pos twe-Tone Photoresists. The ester, carbonate, and ketal acidolysis reactions which form the basis of most positive tone CA resists are thought to proceed under specific acid catalysis (62). In this mechanism, illustrated in Figure 22 for the hydrolysis of tert-huty acetate (type A l) (63), the first step involves a rapid equihbrium where the proton is transferred between the photogenerated acid and the acid-labile protecting group ... 

Historically, simple Vz-alkyl ethers formed from a phenol and a halide or sulfate were cleaved under rather drastic conditions (e.g., refluxing HBr). New ether protective groups have been developed that are removed under much milder conditions (e.g., via nucleophilic displacement, hydrogenolysis of benzyl ethers, and mild acid hydrolysis of acetal-type ethers) that seldom affect other functional groups in a molecule. 

Although many examples of this type of ring system are known in the literature, the vast majority of these are cyclic acetals, which have been used as protecting groups for diols. These have not been included in this chapter. Otherwise, the majority of the compounds which fall into this category are either natural products or derivatives of, or precursors to, the natural products. 

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