Application of the hydrogenphosphonate approach in the synthesis of glycosyl phosphosugars linked through secondary hydroxyl groups

✍ Scribed by Andrey V. Nikolaev; Irena A. Ivanova; Vladimir N. Shibaev; Nikolay K. Kochetkov

• Book ID: 102993648
• Publisher: Elsevier Science
• Year: 1990
• Tongue: English
• Weight: 1002 KB
• Volume: 204
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(90)84021-l

✦ Synopsis

The hydrogenphosphonate approach has been used in syntheses of methyl a-D-mannopyranoside 2-, 3-, and 4-(a-o-mannopyranosyl phosphate), benzyl D-D-galactopyranoside 2-(a-o-mannopyranosyl phosphate), and methyl ,%D-galactopyranoside 4-(a-o-mannopyranosyl phosphate). Condensation of 2,3,4,6tetra-O-benzyl-or 2,3,4,6-tetra-o-benzoyl-a-D-mannopyranosyl hydrogenphosphonate with suitable, partially acylated monohydroxy derivatives in the presence of Me,CCOCI, followed by oxidation of the resulting hydrogenphosphonate diesters with iodine, gave the O-protected phosphate diesters in yields of 67-87%. Deprotection then gave the glycosyl phosphosugars.