Synthèse et étude conformationnelle des quatre méthyl-2-amino-2,4-didésoxy-dl-pentopyranosides
作者:Denis Descours、Dominique Picq、Daniel Anker、Henri Pacheco
DOI:10.1016/s0008-6215(00)81850-9
日期:1982.7
Abstract The four methyl 2-amino-2,4-dideoxy- dl -pentopyranosides were synthesized starting from tetrahydro-2-methoxypyran-3-one. The introduction of a functional group at C-4 of the pyran ring was obtained by formation of the 3-dibenzylenamine derivative, hydroboration, oxidation, and catalytic di- N -debenzylation, giving methyl 2-acetamido-2,4-dideoxy-α- and -β- dl - threo -pentopyranosides. Isomerization
摘要以四氢-2-甲氧基吡喃-3-酮为原料,合成了四种甲基2-氨基-2,4-二脱氧-dl-戊吡喃糖苷。通过形成3-二苄基胺衍生物,进行硼氢化,氧化和催化二-N-脱苄基反应,在吡喃环的C-4处引入官能团,得到甲基2-乙酰氨基-2,4-二脱氧-α。 -和-β-dl-苏-戊吡喃糖苷。在C-3处异构化得到相应的赤型衍生物。通过核磁共振光谱法确定作为O-乙酰化衍生物的四个异构体的构象。