Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of l-2′-“up”-fluoro-4′-thiothymidine

✍ Scribed by Lak Shin Jeong; Hyung Ryong Moon; Su Jeong Yoo; Sun Nan Lee; Moon Woo Chun; Yoong-Ho Lim

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 213 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01021-1

✦ Synopsis

Ring contraction and rearrangement of 4-thiofuranose derivatives were observed through the regioselective opening of the episulfonium ion formed during DAST fluorination in the synthesis of L-2'-"up"-fluoro-4'-thiothymidine.