First Total Synthesis of 1-O-β-D-Glucopyranosyl-5-deoxyadenophorine (I) and Its Aglycon Congener: Determination of the Absolute Configuration.

An improved synthesis of the 5-deoxy-5-(

An improved synthesis of the 5-deoxy-5-(hydroxyphosphinyl)- d-glucopyranoses, and crystal structures of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-[(R)-methoxyphosphinyl]- β-d-glucopyranose and its 5-[(R)-ethylphosphinyl] congener

✍ Thomas Richter; Peter Luger; Tadashi Hanaya; Hiroshi Yamamoto 📂 Article 📅 1989 🏛 Elsevier Science 🌐 English ⚖ 772 KB

Treatment of 3-0-acetyl-5-deoxy-5-(dimethoxyphosphinyl)-l,2-O-isopropylidene-cr-D-glucofuranose (7) with dihydropyran in the presence of pyridinium ptoluenesulfonate gave the 6-0-(tetrahydropyran-2-yl) derivative in 91% yield. Ring-enlargement of this compound by the known, 2-step procedure gave 5-d