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P- tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis

P- tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis

Sachi Asano, Hide-Nori Tanaka, Akihiro Imamura, Hideharu Ishida, Hiromune Ando

Org Lett. 2019 Jun 7;21(11):4197-4200.

PMID: 31145627

Abstract:

Aromatic protective groups are widely used in carbohydrate synthesis owing to their numerous merits. However, they unpredictably make certain compounds insoluble in organic solvents owing to their π-stacking abilities. It was found that introducing a tert-butyl group onto the aryl moiety improves the solubility of highly insoluble carbohydrate derivatives, such as those of N-acetylglucosamine. In this study, tert-butyl-substituted aromatic protecting groups are demonstrated to work as well as the original unsubstituted form, while improving the efficiency of glycosylations.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42411004	Butyl p-aminobenzoate-Agarose			Price

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