| 王晓茵,王鹏,侯斌,等.a-(1→2)-甘露糖三糖的合成[J].中国海洋药物,2015,34(6):69-74. |
| a-(1→2)-甘露糖三糖的合成 |
| Synthesis of a-(1→2)-Mannotrisacchride |
| 投稿时间：2015-03-10 修订日期：2015-04-09 |
| DOI： |
| 中文关键词: a -(1→2)-甘露糖三糖 硫苷 N-对甲苯磺酰亚胺酯 糖苷化 |
| English Keywords:a-(1→2)-Mannotrisacchride Thiolglycoside donor N-tosyl benzimidate glycosylation |
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| 中文摘要: |
| 目的 利用化学方法高效合成PI-88糖基片段a -(1→2)-甘露糖三糖。方法 以4,6位苯亚甲基保护的D-甘露糖硫苷3为原料合成N-对甲苯磺酰亚胺酯供体6,以TMSOTf作为促进剂,供体6与受体3进行糖苷化反应,得到a -(1→2) 甘露糖二糖7,然后将二糖脱除苯甲酰基,再次与供体7进行糖苷化反应,合成出PI-88糖基片段a -(1→2) 甘露糖三糖2。 结果 以85%和79%的糖苷化反应产率,得到PI-88类似物a -(1→2) 甘露糖三糖2,为PI-88构效关系的研究提供物质基础和保障。 |
| English Summary: |
| Objective An efficient synthesis of a-(1→2)-Mannotrisacchride was achieved. The target was designed to mimic the promising anticancer agent PI-88. Method The glycosyl N-tosyl benzimidate 6 was synthesized from phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl) -1-thio-a-D- mannopyranoside 3. The analogue 2 was obtained from the glycosyl N-tosyl benzimidate 6 with acceptor 8 in the presence of TMSOTf at 0 oC. Results The desired oligasacchride was obtained in a satisfying yield, which was valuable for studying the structure and activity relationship of PI-88. |
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