A novel route to 1,4-anhydro derivatives of β-d-galactopyranose

✍ Scribed by Clive Bullock; Leslie Hough; Anthony C. Richardson

• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 604 KB
• Volume: 197
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(90)84136-i

✦ Synopsis

Treatment of 1-0-acetyl-4-0-mesyl derivatives of a-o-glucopyranose with sodium azide in N,N-dimethylformamide gave 1,4-anhydro derivatives of P-D- galactopyranose and not the expected 4-azides. 1,4-Anhydro-6-azido-2,3-di-Obenzoyl-6-deoxy+-D-galactopyranose was converted into the corresponding 6bromide, using hydrogen bromide in glacial acetic acid. Similar treatment of 6azido-and 4,6-diazido-hexoses leads to rapid and specific substitution of the 6-azide by bromide in each case. RESULTS AM) DISCUSION Nucleophilic substitution of the 1-0-acetyl-4,6-di-0-mesyl derivative 2 with azide, followed by conversion into the l-bromide 4 and subsequent phosphoryla-*Preliminary communication: see ref. 8.