Reactions of 3-O-acetyl-2-C-p-tolylsulfonyl-D-Arabino- and -D-ribo-hex-1-enitol derivatives with nucleophiles; the SN2′ mechanism is proved firstly in glycal derivatives

✍ Scribed by Sakakibara Tohru; Takaib Izumi; Yamamoto Azuma; Iizuka Hiroyuki; Hirasawa Kohji; Ishido Yoshiharu

• Book ID: 104228718
• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 254 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97461-6

✦ Synopsis

Reactions of the title compounds with sodium methoxide and sodium borodeuteride were found to proceed mainly via the SK2' mechanism; nucleophiles selectively attacked the anomeric carbon atom from the same side of the leaving acetoxyl group at C-3.