Synthesis of kanamycin a analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-d- and -l-glycero-hexopyranose
作者:Ryuji Kuwahara、Tsutomu Tsuchiya
DOI:10.1016/0008-6215(96)00051-1
日期:1996.6
6-Azido-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranoses were synthesized in five steps from (2S)-and (2R)-1,2-O-isopropylideneglycerols, respectively. After conversion into the corresponding ethyl 1-thioglycosides, each was condensed with a protected derivative of 6-O-(3-amino-3-deoxy-alpha-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation
由(2S)-和(2R)-1,2-O-异亚丙基甘油分5个步骤合成了6-叠氮基3-oxa-2,3,4,6-四脱氧-D-和-L-甘油己糖分别。在转化成相应的乙基1-硫代糖苷之后,将它们各自与6-O-(3-氨基-3-脱氧-α-D-吡喃葡萄糖基)-2-脱氧链胺的保护的衍生物缩合(16)。缩合产物的脱保护和叠氮基的还原得到标题化合物。