Abstract
“Pseudo-sugar” is the name of a class of compounds in which a ring-oxygen of a hexopyranoid sugar is replaced by a methylene group. There are thirty-two theoretically possible stereoisomers in the pseudo-sugar family, including anomer-like compounds. The first pseudo-sugar was synthesized by G. E. McCasland and his coworkers in 1966. The most accessible starting material for the synthesis of pseudo-sugars was the Diels-Alder adduct of furan and acrylic acid. The Diels-Alder adduct was readily resolved by means of optically active amines as resolution reagents into the two antipodes, which were then used as starting compounds for the synthesis of enantiomeric pseudo-sugars. Also, a chiral synthesis from true sugars has been used for the preparation of enantiomeric pseudo-sugars.
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