Experiment 5: SYNTHESIS OF A PROTECTED MONOSACCHARIDE Learning outcomes Reflux set up • Rotavap • Solubility and crystallization Behaviour of molecules on TLC plates Background Since carbohydrates are polyfunctional compounds, the chemical synthesis - even of the most simple derivatives - requires the application of protecting groups. Essentially, the protecting groups employed in the chemistry of carbohydrates are the same as those generally used in organic chemistry. However, the polyfunctionality (presence of a large number of the same functional group) - which is mainly the hydroxy group at the carbohydrate skeletons, necessitates specific protecting group manipulations, including introduction of ester, ether, and acetal groups, their removal or occasional migration and various additional transformations. OMe OMe HO HO OH HO OMe H® HO- HO OMe

Experiment 5: SYNTHESIS OF A PROTECTED MONOSACCHARIDE Learning outcomes Reflux set up • Rotavap • Solubility and crystallization Behaviour of molecules on TLC plates Background Since carbohydrates are polyfunctional compounds, the chemical synthesis - even of the most simple derivatives - requires the application of protecting groups. Essentially, the protecting groups employed in the chemistry of carbohydrates are the same as those generally used in organic chemistry. However, the polyfunctionality (presence of a large number of the same functional group) - which is mainly the hydroxy group at the carbohydrate skeletons, necessitates specific protecting group manipulations, including introduction of ester, ether, and acetal groups, their removal or occasional migration and various additional transformations. OMe OMe HO HO OH HO OMe H® HO- HO OMe

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter25: Carbohydrates

Section: Chapter Questions

Problem 25.48P

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