Protecting groups play an important role in regio- and stereo- chemical control within synthetic carbohydrate chemistry. Nevertheless, the implementation and optimization of protecting groups in carbohydrate synthesis are underdeveloped compared to protein and nucleotide synthesis. As an example, silyl ether protecting groups such as triiosopropylsilyl (TIPS) and tert-butyldiphenylsilyl (TBDPS) ethers are underutilized due to their bulky nature despite their importance more broadly in organic synthesis. In nucleoside chemistry, this problem has been successfully solved using a suitable spacer (CH2O) between the nucleoside and the silyl group. This minimizes the steric demand of the TOM (CH2OTIPS) protecting group in nucleoside chemistry. However, the TOM protecting group was found to be unsatisfactory under a variety of standard carbohydrate chemistry reaction sequences. In this disclosure, a methoxy (CH2O) spacer has been used in conjunction with several bulky silyl groups to protect the hydroxyl groups of carbohydrates. Initial studies show that these novel alcohol protecting groups can be introduced into complex carbohydrate building blocks as temporary or permanent protecting groups, and good stereoselectivity can be achieved in glycosylation reactions.

Extending the use of silyl protecting groups in carbohydrate chemistry

256th National Meeting (2018)

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