Synthesis of cyclopropanated and branched-chain pyranosides via carbohydrate triflates

✍ Scribed by Fatima, Ayjaz ;Zaman, Fakhar ;Shekhani, Mohammed Saleh ;Malik, Abdul ;Voelter, Wolfgang

• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 419 KB
• Volume: 1990
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199019900173

✦ Synopsis

Abstract

Approaches to the cyclopropanated pyranosides benzyl 3,4‐(“exo”‐cyano)methano‐3,4‐dideoxy‐β‐(L‐arabinopyranoside (5) and benzyl 3,4‐(“exo”‐cyano)methano‐3,4‐dideoxy‐α‐D‐arabinopyranoside (6) and the branched‐chain epoxy sugars benzyl 2,3‐anhydro‐4‐(tert‐butoxycarbonyl)methyl‐4‐deoxy‐β‐L‐lyxopyranoside (7) and benzyl 2,3‐anhydro‐4‐(tert‐butoxycarbonyl)‐methyl‐4‐deoxy‐α‐D‐lyxopyranoside (8) by displacement of the triflate group with carbanions are described. Preparation of biologically important sugars bearing peptides has been demonstrated by reduction of 5 and 6 to benzyl 3,4‐(“exo”‐aminomethyl)methano‐3,4‐dideoxy‐α‐L‐arabinopyanoside (9) and benzyl 3,4‐(“exo”‐aminomethyl)methano‐3,4‐dideoxy‐α‐D‐arabinopyranoside (10) and the coupling of the resulting amines with protected L‐alanine.