Takeo K, Kitamura S, Murata Y
Department of Agricultural Chemistry, Kyoto Prefectural University, Japan.
Carbohydr Res. 1992 Feb 7;224:111-22. doi: 10.1016/0008-6215(92)84098-d.
Nigerose [alpha-D-Glcp-(1----3)-D-Glcp], nigerotriose, nigerotetraose, and nigeropentaose have been synthesized by chain elongation starting at the reducing end, from the corresponding octa-, undeca-, tetradeca-, and heptadeca-beta-D-acetates, respectively, via thioglycoside-mediated 1,2-cis coupling, using 1,2,4,6-tetra-O-acetyl-beta-D-glucopyranose as the glucosyl acceptor and methyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside, methyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside, and methyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1----3)-2,4,6-tri-O- benzyl-1-thio-beta-D-glucopyranoside as the donors.
黑曲霉糖[α-D-葡萄糖吡喃糖基-(1→3)-D-葡萄糖吡喃糖]、黑曲霉三糖、黑曲霉四糖和黑曲霉五糖已分别从相应的八-O-乙酰基-β-D-葡萄糖、十一-O-乙酰基-β-D-葡萄糖、十四-O-乙酰基-β-D-葡萄糖和十七-O-乙酰基-β-D-葡萄糖开始，通过硫代糖苷介导的1,2-顺式偶联，以1,2,4,6-四-O-乙酰基-β-D-吡喃葡萄糖作为葡萄糖基受体，以及以2,3,4,6-四-O-苄基-1-硫代-β-D-吡喃葡萄糖苷甲酯、3-O-烯丙基-2,4,6-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷甲酯和O-(2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基)-(1→3)-2,4,6-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷甲酯作为供体，从还原端开始进行链延长合成得到。
