Formation, and stereochemistry, of 1,2-O-(1-methyl-1,2-ethanediyl)-d-glucose acetals formed in the acid-catalyzed hydrolysis of O-(2-hydroxypropyl)cellulose
作者:Dae-Sil Lee、Arthur S. Perlin
DOI:10.1016/0008-6215(84)85129-0
日期:1984.3
Abstract In the hydrolysis of O -(2-hydroxypropyl)cellulose, residues of d -glucose substituted with a single O -(2-hydroxypropyl) substituent at O-2 (irrespective of the pattern of additional substitution at O-3 or O-6) form 1,2- O -(1-methyl-1,2-ethanediyl)-α- d -glucose acetals. Based on the characteristics of 2- O -(2-hydroxypropyl)- d -glucose and derivatives thereof in aqueous acid, these bicyclic
摘要在O-(2-羟丙基)纤维素的水解过程中,d-葡萄糖残基在O-2处被单个O-(2-羟丙基)取代基取代(与在O-3或O-处的附加取代方式无关) 6)形成1,2-O-(1-甲基-1,2-乙二基)-α-d-葡萄糖缩醛。基于2-O-(2-羟丙基)-d-葡萄糖及其在酸性水溶液中的衍生物的特性,这些双环产物显示出包含两种呋喃糖和两种吡喃糖种类的混合物,它们的相对稳定性差异很大,具体取决于该化合物的1,4-二恶烷环的C-8的手性。稳定性的顺序是1,2- O-[1-甲基-(R)-1,2-乙二基]-α-d-吡喃葡萄糖> 1,2- O-[1-甲基-(S)-1 2-乙二基]-α-d-葡糖呋喃糖> 1,2- O-[1-甲基-(S)-1,2-乙二基]-α-d-吡喃葡萄糖> 1,2- O-[1-甲基- (R)-1,2-乙二基]-α-d-葡萄糖呋喃糖。Nmr证据表明这两种吡喃糖衍生物具有“ H-inside”构象。尽