Chemistry of 1,1-bis(acylamido)-1-deoxyalditols. Base-catalyzed, intramolecular O,N-transacylation of per-O-acyl-1,1-bis(benzamido)-1-deoxy-d-glucitols in aprotic solvents
✍ Scribed by Irene Pallares; María E. Gelpi; Raúl A. Cadenas
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- English
- Weight
- 957 KB
- Volume
- 111
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Penta-0-acetyl and penta-U-propanoyl derivatives of l,l-bis(benzamido)-ldeoxy-D-ghtcitol are transformed into 1-acetamido-1-benzamido-1-deoxy-D-glucitol and 1-benzamido-1-deoxy-l-propanamido-D-glucitol, respectively, by heating with a suspension of potassium cyanide in acetonitrile, and subsequently O-deacylating with sodium methoxide in methanol. The reaction was also studied in the presence of a crown ether. When other nucleophiles (HO-and CH,O-) or other aprotic solvents (propanonitrile, benzene) were employed, the yields of transacylation products diminished noticeably; likewise, the use of sodium as the counter-ion significantly affected this reaction. These results are qualitatively discussed in terms of the solvent effects on the reactivity of the nucleophiles employed.