A versatile C–5 synthon – Ethyl–3–[(4R)–2,2–dimethyl–1,3–dioxolan–4–yl]–2,2–difluoro–3–hydroxypropanoate in high ch

Salman Mukarram; Hemant V. Chavan; Imtiyaz Khan; Babasaheb P. Bandgar

Volume : IV, Issue : II, February - 2014

A versatile C–5 synthon – Ethyl–3–[(4R)–2,2–dimethyl–1,3–dioxolan–4–yl]–2,2–difluoro–3–hydroxypropanoate in high ch

Salman Mukarram, Hemant V. Chavan, Imtiyaz Khan, Babasaheb P. Bandgar

Abstract :

A practical and efficient protocol is described for the synthesis of ethyl-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-difluoro-3-hydroxypropanoate (2), which is an important intermediate for the preparation gemcitabine hydrochloride. Literature survey reveals that this diastereomer exists with its other stereomer ethyl 3-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-difluoro-3-hydroxypropanoate in 3:1 ratio. Our observations on differences in physical properties of diastereomers lead us to purify and characterize this important diastereomer in high optical purity that could be readily adaptable on industrial scale.