The synthesis of chlorodeoxyhexofuranoid derivatives

✍ Scribed by Haralambos Parolis

• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 749 KB
• Volume: 114
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88169-5

✦ Synopsis

The reaction of 1,2-O-isopropylidene-cc-D-glucofuranose with sulfuryl chloride at 0' and at 50' afforded 6-chloro-6-deoxy-1,2-O-isopropylidene-a-D-glucofuranose 3,5-bis(chlorosulfate)

(3) and 5,6-dichloro-5,6-dideoxy-1,2-O-isopropylidene+Lidofuranose 3-chlorosulfate (7, not characterised), respectively. Dechlorosulfation of 3 afforded the hydroxy derivative, whereas treatment of 3 with pyridine gave the 3,5-(cyclic sulfate).