A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose from a Ferrier derivative of tri-O-acetyl-d-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958)

Hayato Okazaki, Kengo Hanaya, Mitsuru Shoji, Noriyasu Hada, Takeshi Sugai

研究成果: Article査読

14 被引用数 (Scopus)

抄録

A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose (4-O-methylManNAc), the chemo-enzymatic precursor of 7-O-methylsialic acid and laninamivir, was established. Known p-methoxyphenyl 6-O-(tert- butyldimethylsilyl)-2,3-dideoxy-α-d-erythro-hex-2-enopyranoside was the starting material, and it was derived via Ferrier reaction from tri-O-acetyl-d-glucal. The total yield was 43% over six steps from the starting material. As the key steps, Payne oxidation provided a syn-epoxy alcohol, and the inversion from an aziridine to an oxazoline proceeded stereoselectively. Although the ring opening reaction of the epoxide with an azide gave both the 2- and 3-azido regioisomers, they could be merged into the desired aziridine via independent routes.

本文言語English
ページ(範囲)7931-7935
ページ数5
ジャーナルTetrahedron
69
37
DOI
出版ステータスPublished - 2013 9 16

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「A new route toward 2-acetamido-4-O-methyl-2-deoxy-d-mannopyranose from a Ferrier derivative of tri-O-acetyl-d-glucal, which contributes to aldolase-catalyzed synthesis of laninamivir (CS-8958)」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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