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Facile Preparation of L-Iduronic Acid and α-L-Iduronidation Using Methyl 1,2,3,4-Tetra-O-acetyl-α-L-iduronate as Glycosyl Donor

Chemical and Pharmaceutical Bulletin, ISSN: 1347-5223, Vol: 71, Issue: 9, Page: 724-729
2023
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Article Description

Methyl 1,2,3,4-tetra-O-acetyl-α-L-iduronate was prepared from methyl 1,2,3,4-tetra-O-β-D-glucuronate in two steps: Ferrier’s photobromination and subsequent radical reduction with tris(trimethylsilyl)silane. The obtained methyl 1,2,3,4-tetra-O-acetyl-α-L-iduronate was a good glycosyl donor for the L-iduronidation when bis(trifluoromethanesulfonic)imide was employed as the activator. The reaction afforded the α-isomer as the major product, the configuration of which is the same as that of the L-iduronic acid unit in heparin and heparan sulfate.

Bibliographic Details

Kajimoto, Tetsuya; Du, Tianqi; Yoshitake, Tenchi; Kaneko, Kimiyoshi; Kobayashi, Hiroya; Matsushima, Yasuyuki; Miura, Tsuyoshi

Pharmaceutical Society of Japan

Chemistry; Pharmacology, Toxicology and Pharmaceutics

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