Synthetic applications of ortho esters

Abstract

Abstract

The hydrolysis of geminal ethers: a kinetic appraisal of orthoesters and ketals

“…Consistent with this, the X-ray crystal structure of an analogous yet conformationally constrained bicyclic orthoester possesses an unusually elongated axial C─O bond ( Fig. 2 ), which undergoes preferential cleavage with Lewis acids [ 31 ]. The Cambridge Structural Database (2015) [ 32 ] contains a single example of a five-membered 1,3-dioxolane orthoester [ 33 ].…”

myo-Inositol 1,3-acetals as early intermediates during the synthesis of cyclitol derivatives

“…Preparation and use of 1,3-acetals of polyols and carbohydrates, other than inositols, have been reported. [29][30][31][32][33][34][35][36] However, as expected, such instances are relatively rare compared to those of 1,2-acetals. Since acetalization of myo-inositol leads to the formation of at least three isomeric products (and perhaps oligomeric acetals as well) the isolated yield of each of these acetals is seldom more than 35%.…”

Anodic Oxidation of Dithiane Carboxylic Acids: A Rapid and Mild Way to Access Functionalized Orthoesters

“…Scheme 1. Common reactions using orthoesters Orthoesters are highly reactive compounds that have found many applications in synthesis such as diol protecting groups, 1 acylating agents, 2 Claisen rearrangement reagents 3 or coupling partners in heterocyclic chemistry (Scheme 1). [4][5][6] Orthoesters have also found applications in medicinal chemistry.…”