2-O-苄基-3,5-内醚-α和β-D-木呋喃甲基甙的合成  

Synthesis of Methyl 2-O-Benzyl-3,5-Anhydro-α-and β-D-Xylofuranoside

作　　者：曹玲华[1] 刘育亭[1] Cao Lingbua;Liu Yuting(Department of Chemistry,Xinjiang University,Wulumuqi)

机构地区：[1]新疆大学化学系

出　　处：《高等学校化学学报》1985年第3期225-228,共4页Chemical Journal of Chinese Universities

摘　　要：本文报导一对具有2,6-二氧杂双环[3.2.0]庚烷骨架的四元环内醚型戊糖甙差向异构体的合成.其关键化合物2-O-苯甲基-3,5-二-O-对甲苯磺酰基-α-和β-D-木呋喃甲基甙(S)、2-O-苯甲基-5-O-对甲苯磺酰基-α-D-木呋喃甲基甙及其3-O-乙酰基衍生物均以结晶形固体制得,由这些结晶分别制得标题化合物.The title compounds with the 2, 6-dioxabicyclo-[3.2.0]-heptane skeleton were synthesized respectively from methyl 3,5-O-(1-methylethylidene)-α- and β-D-xylofuranoside (IA and IB) in five steps. This consists of benzylation, deacetonation, tosylation, acetylation and ring closure. Then the eight intermediates i.e. methyl 2-O-benzyl-3,5-O-(1-methylethylidene)-α- and β-D-xylofuranoside (ⅡA, ⅡB), methyl 2-O-benzyl-α- and β-D-xylofuranoside (ⅢA, ⅢB), methyl 2-O-benzyl-3, 5-di-O-tosyl-β-D-xylofuranoside (ⅣB), methyl 2-O-benzyl-3-O-acetyl-5-O-tosyl-a-D-xylofuranoside ( Ⅵ A), methyl 2-O-benzyl-3, 5-anhydro-α- and β-D-xylofuranoside (ⅦA, ⅦB)were obtained sequentially. The key intermediates both Ⅳ A and Ⅵ B are crystalline. The mass spectra of these compounds have been given.

关 键 词：差向异构体 苯甲基 标题化合物 呋喃 庚烷 四元环 乙酰基 

分 类 号：O62[理学—有机化学]