A highly stereoselective route to 1-C-(2-hydroxyaryl)-alditol derivatives

✍ Scribed by Giovanni Casiraghi; Mara Cornia; Giovanna Gasparri Fava; Marisa Ferrari Belicchi; Lucia Zetta

• Book ID: 102990075
• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 682 KB
• Volume: 186
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(89)84035-2

✦ Synopsis

Arylation at C-l of 2,3:4,5-di-0-isopropylidene-~arabinose and 4-O-benzyl-2,3-O-isopropylidene-D-threose variously using titanium or magnesium salts of 4tert-butylphenol, 2-naphthol, and 5-pentylresorcinol gave the epimeric l-c-arylalditol derivatives.

One of these derivatives, namely, 1-C-(3-tert-butyl-6-hydroxyphenyl)-2,3:4,5-di-O-isopropylidene-D-gluco-pentitol, forms a crystalline 1:3 inclusion compound with 4-tert-butylphenol, the structure of which, established by X-ray diffraction, shows that guest molecules are linked through hydrogen bonds to the hydrophilic cavity created by the helical chains of the hosts.