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Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5'-alkynylation.

ABSTRACT: The 5'-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2',3'-di-O-protecting groups (R¹): O-alkyl groups led to modest diastereoselectivities (65:35) in favor of the 5'R-isomer, whereas O-silyl groups promoted higher diastereoselectivities (up to 99:1) in favor of the 5'S-isomer. A study related to this protecting group effect on the diastereoselectivity is reported.

SUBMITTER: Ben Othman R

PROVIDER: S-EPMC5550804 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5'-alkynylation.

Ben Othman Raja R Fer Mickaël J MJ Le Corre Laurent L Calvet-Vitale Sandrine S Gravier-Pelletier Christine C

Beilstein journal of organic chemistry 20170804

The 5'-alkynylation of uridine-derived aldehydes is described. The addition of alkynyl Grignard reagents on the carbonyl group is significantly influenced by the 2',3'-di-O-protecting groups (R1): O-alkyl groups led to modest diastereoselectivities (65:35) in favor of the 5'R-isomer, whereas O-silyl groups promoted higher diastereoselectivities (up to 99:1) in favor of the 5'S-isomer. A study related to this protecting group effect on the diastereose ...[more]

PMID: 28845198

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