A Clean Conversion of D-Glucosamine Hydrochloride to a Pyrazine in the Presence of Phenylboronate or Borate

✍ Scribed by Jan Rohovec; Jan Kotek; Joop A. Peters; Thomas Maschmeyer

• Book ID: 101348114
• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 209 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200110)2001:20<3899::aid-ejoc3899>3.0.co;2-g

✦ Synopsis

D-Glucosamine was found to undergo a condensation to give 2-(arabo-tetrahydroxybutyl)-5-(erythro-2,3,4-trihydroxybutyl)-pyrazine (2) as practically the sole product in the presence of phenylboronate or borate. The reaction proceeds in aqueous solutions at room temperature in 3 h in 58% isolated