153289-67-9Relevant academic research and scientific papers
Preparation of various C-2 branched carbohydrates using intramolecular radical reactions
Choe, Sung Won Tina,Jung, Michael E
, p. 731 - 744 (2000)
A new and efficient method for the facile synthesis of C-2 branched carbohydrates has been developed using an intramolecular radical cyclization-fragmentation reaction. The desired C-2 branched glucopyranosides were isolated in 40-84% yield. Additionally, an unexpected furanoside was obtained from a tributyltin iodide-promoted rearrangement of the radical intermediate. The C-2 formyl glycal was also isolated in good yield using tris(trimethylsilyl)silane (TTMSS) as the reducing agent. This method was extended to synthesize a β C-2 branched glucopyranoside, a C-2 branched galactoside and a C-2 cyano glucopyranoside.
STEREOSPECIFIC INTRAMOLECULAR FORMYL TRANSFER VIA RADICAL CYCLIZATION-FRAGMENTATION: PREPARATION OF ALKYL 2-DEOXY-2α-FORMYLGLUCOPYRANOSIDES AND SIMILAR COMPOUNDS
Jung, Michael E.,Choe, S. W. Tina
, p. 6247 - 6250 (2007/10/02)
An efficient synthesis of alkyl-2-deoxy-2α-formylglucopyranosides is described.The key step involves a novel stereospecific intramolecular formyl transfer via a radical cyclization-fragmentation process in good yield.
