Synthesis of a cycloheptaose consisting of (1 → 4)-linked 7-amino-6,7-dideoxy-α-d-gluco-heptopyranosyl units: A new analog of cyclomaltoheptaose

✍ Scribed by Hans H. Baer; Yaping Shen; Francisco Santoyo González; Antonio Vargas Berenguel; Joaquin Isac García

• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 888 KB
• Volume: 235
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)80083-d

✦ Synopsis

Approaches to chain extension at the C-6 positions in cyclomaltoheptaose (1) were examined with the aim of producing novel /3-cyclodextrin analogs composed of heptose or hepturonic acid units. Iron carbonyl-mediated methoxycarbonylation, and nucleophilic displacement by cyanide, in the fully acetylated heptakisf6-deoxy-6-iodo) and heptakisf6-0-mesyl) derivates of 1, respectively, were unsuccessful, as were similar reactions attempted with the newly synthesized, analogous allyl-protected derivatives of 1. However, reaction of unprotected heptakis(6-deoxy-6-iodokyclomaltoheptaose with lithium cyanide in N,N-dimethylformamide afforded a high yield of the corresponding heptaki.s(6-cyano-6-deoxy) compound, namely, cyclohepta-fl -+ 4)_(6-deoxya-p-gluco-heptopyranosid)urononitrile, catalytic hydrogenation of which gave the title compound, cycle-(1 --f 4)-(7-amino-6,7-dideoxy-a_D-&coheptopyranojheptaose, isolated as its peracetyl derivative.