Kuwahara R, Tsuchiya T
Institute of Bioorganic Chemistry, Kawasaki, Japan.
Carbohydr Res. 1996 Jun 5;286:107-22. doi: 10.1016/0008-6215(96)00051-1.
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 products gave the title compounds.
6-叠氮基-3-氧杂-2,3,4,6-四脱氧-D-和-L-甘油基己吡喃糖分别由(2S)-和(2R)-1,2-O-异丙叉甘油经五步合成。在转化为相应的乙基硫代糖苷后，每种都与6-O-(3-氨基-3-脱氧-α-D-吡喃葡萄糖基)-2-脱氧链霉胺(16)的保护衍生物缩合。缩合产物的叠氮基去保护和还原得到标题化合物。
