Synthesis of Methyl-3,4-Dideoxy-α(β)-D-glycero-hex-3-enopyranosiduloses from Levoglucosenone

Autor:	L. Kh. Faizullina, Yu. S. Galimova, Yu. A. Khalilova, Farid A. Valeev
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Acetic anhydride Ethanol chemistry Organic Chemistry Methanol Bridge (interpersonal) Medicinal chemistry
Zdroj:	Russian Journal of Organic Chemistry. 57:1047-1052
ISSN:	1608-3393 1070-4280
Popis:	Opening of the 1,6-anhydro bridge in levoglucosenone by the action of acetic anhydride in the presence of ZnCl2 afforded diastereoisomeric 1,6-di-O-acetyl-3,4-dideoxy-α/β-D-glycero-hex-3-enopyranos-2-uloses, and alcoholysis of the resulting diacetates in methanol, ethanol, and propan-2-ol in the presence of p-toluenesulfonic acid, camphor-10-sulfonic acid, ZnCl2, and HCl was studied. Their methanolysis in the presence of CSA gave methyl 3,4-dideoxy-α/β-D-glycero-hex-3-enopyranosid-2-uloses that are precursors to purpurosamine C and (+)-frontalin.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3c6037d94687c7ff7991b7a94fafd397 https://doi.org/10.1134/s1070428021070034 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.