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Synthesis of ?-C-galactosyl D- and L-alanines.

ABSTRACT: Synthesis of ?-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and S(N)2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.

SUBMITTER: Thota VN

PROVIDER: S-EPMC4492545 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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Synthesis of β-C-galactosyl D- and L-alanines.

Thota V Narasimharao VN Gervay-Hague Jacquelyn J Kulkarni Suvarn S SS

Organic & biomolecular chemistry 20121001 40

Synthesis of β-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and S(N)2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds. ...[more]

PMID: 22961309

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