Partial benzoylation of 1,5-anhydroxylitol

✍ Scribed by Yôtaro Kondo

• Book ID: 102640768
• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 307 KB
• Volume: 111
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88317-7

✦ Synopsis

In previous publications on the selective benzoylation of methyl 6-deoxy-/I-Dglucopyranoside', 1,5-anhydro-4,6-O-beruylidene-D-glucito12, and 1,5-anhydro-D-glucito13, we reported that, among the secondary hydroxyl groups, the 3-hydroxyl groups are the most reactive. In connection with these studies, this communication describes the partial benzoylation of 1,5-anhydroxylitol (1).

Treatment of 1 with one molar equivalent of benzoyl chloride in pyridine at -40" gave a complex mixture, shown by quantitative t.1.c. to consist of the 2,3,4tribenzoate 2 (1.6x), the 2,4_dibenzoate 3 (14.5 %), the 2,3-dibenzoate 4 (30.1x), the 3-benzoate 5 (16.6x), and the 2-benzoate 6 (37.2%).

After chromatographic separation, the structure of 2 was established by comparison with an authentic specimen prepared from 1 with an excess of benzoyl