Motawia M S, Olsen C E, Denyer K, Smith A M, Møller B L
Department of Plant Biology, The Royal Veterinary and Agricultural University, Copenhagen, Denmark.
Carbohydr Res. 2001 Feb 15;330(3):309-18. doi: 10.1016/s0008-6215(00)00306-2.
The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4'-OH group or by reversing its configuration, is reported. For synthesis of the 4'-O-acetylated analog, beta-maltose was converted into its per-O-benzylated-4',6'-O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6'. Acetylation at C-4' of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra-O-benzyl-alpha/beta-D-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog.
报道了作为麦芽糖类似物的标题化合物的化学合成，其中非还原端通过4'-OH基团的乙酰化或通过反转其构型进行修饰。为了合成4'-O-乙酰化类似物，将β-麦芽糖转化为其全-O-苄基化-4',6'-O-亚苄基衍生物，随后除去亚苄基缩醛官能团并在C-6'处进行选择性甲硅烷基化。对所得甲硅烷基化化合物的C-4'进行乙酰化，随后除去苄基醚保护基并进行脱甲硅烷基化，得到所需的类似物。另一种麦芽糖类似物是通过糖基供体O-(2,3,4,6-四-O-苄基-α/β-D-吡喃半乳糖基)三氯乙酰亚胺酯与糖基受体苯基2,3,6-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷之间的糖苷化反应合成的，随后除去苯硫基并进行脱苄基化以提供所需的类似物。
