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Synthesis of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-C-[(RS)-ethylphosphinyl]-.alpha.- and .beta.-D-glucopyranoses and their structural analysis by 400-MHz proton nuclear magnetic resonance

โœ Scribed by Yamamoto, Hiroshi; Yamamoto, Keizo; Inokawa, Saburo; Yamashita, Mitsuji; Armour, Margaret Ann; Nakashima, Tom T.


Book ID
126091955
Publisher
American Chemical Society
Year
1983
Tongue
English
Weight
661 KB
Volume
48
Category
Article
ISSN
0022-3263

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An improved synthesis of the 5-deoxy-5-(
โœ Thomas Richter; Peter Luger; Tadashi Hanaya; Hiroshi Yamamoto ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ English โš– 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