Studies on Acetylenic Compounds. XXIX. A New Method for Synthesis of DL-Ribose.

Issei Iwai; Tadahiro Iwashige; Motoji Asai; Kazuo Tomita; Tetsuo Hiraoka; Junya Ide

doi:10.1248/cpb.11.188

Issei Iwai, Tadahiro Iwashige, Motoji Asai, Kazuo Tomita, Tetsuo Hiraoka, Junya Ide

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JOURNAL FREE ACCESS

1963 Volume 11 Issue 2 Pages 188-192

DOI https://doi.org/10.1248/cpb.11.188

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Abstract

DL-Ribose was synthesized stereospecifically by oxidative hydroxylation of 2-ethoxy-5-(tetrahydro-2-pyranyloxy) methyl-2, 5-dihydrofuran (VII), which was obtained by hydrogenation of DL-1, 1-diethoxy-5-(tetrahydro-2-pyranyloxy)-2-pentyn-4-ol. DL-1, 1-diethoxy-5-(tetrahydro-2-pyranyloxy)-2-pentyn-4-ol was prepared by the Grignard reaction of (tetrahydro-2-pyranyloxy)acetaldehyde with propargyl diethyl acetal magnesium bromide.

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