N-(3,4,6-Tri-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)succinimid | 99694-26-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(3,4,6-Tri-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)succinimid
• 英文别名: [(2R,3R,4S,5S,6S)-3,4-diacetyloxy-6-(2,5-dioxopyrrolidin-1-yl)-5-iodooxan-2-yl]methyl acetate
• CAS: 99694-26-5
• 化学式: C₁₆H₂₀INO₉
• 分子量: 497.241
• InChiKey: LDYWHAAQASFBNO-XNNBJJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  125.51
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  N-碘代丁二酰亚胺 、 乙酰化葡萄烯糖 以 乙腈 为溶剂， 反应 72.0h， 以70%的产率得到N-(3,4,6-Tri-O-acetyl-2-desoxy-2-iod-α-D-mannopyranosyl)succinimid
  参考文献：
  名称：

  制备脱氧糖类固醇糖苷的研究

  摘要：

  在立体选择性反应，所述烯糖1，2和8可被冷凝与胆固醇和洋地黄毒苷，以得到2-脱氧-2-碘-α糖苷3，4，5和9由N-碘代琥珀酰亚胺处理。在缓慢的反应中，直接的N-碘代琥珀酰亚胺加合物如6作为副产物出现。在丁酮中，11仅部分反应以分别产生预期的糖苷12和13，优选形成hex-2-enopyranosides 17和18也可以通过Ferrier重排获得。它们的结构在光谱和加氢（至20）条件下得到了证明。所述cardenolide苷10，14和15可以通过hydrogenative分裂掉碘来获得。用洋地黄毒苷原酸催化的三乙酰基洋地黄糖21的糖基化反应以约2：3的比例产生α-和β-异头物10和25，最大产率为50％。较高的温度增加了β-组分的相对比例，产率急剧下降。乙酰溴代肟糖22的糖基化 用不同的银盐也可以得到大约50％的异头物比率，即α：β= 2：3。

  DOI：

  10.1002/jlac.198519851105

文献信息

• Stereoselective synthesis of 2-deoxy-?-d-arabino-hexopyranosides of triterpene alcohols
  作者：L. A. Baltina、O. B. Flekhter、E. V. Vasil'eva、G. A. Tolstikov

  DOI：10.1007/bf01430746

  日期：1996.9

  Abstract2-Deoxy-2-iodo-α-d-mannopyranosides of triterpene alcohols of the oleanane series were synthesized inca. 60% yields by glycosylation with readily accessibled-glucal triacetate in the presence ofN-iodosuccinimide as the promotor. Their deiodination by catalytic hydrogenation followed by deacetylation yielded 2-deoxy-α-d-arabino-hexopyranosides of glycyrrhetic acid derivatives and allobetulin

  摘要合成了齐墩果烷系列三萜醇的2-脱氧-2-碘-α-d-吡喃甘露糖苷。在作为启动子的 N-碘代琥珀酰亚胺存在下，通过使用易于接近的三乙酸葡糖酯进行糖基化，产率为 60%。它们通过催化氢化脱碘，然后去乙酰化产生甘草次酸衍生物和异白素的 2-脱氧-α-d-阿拉伯-吡喃己糖苷。
• The Synthesis of the 2- and 2'-Monodeoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose
  作者：Hans Peter Wessel、Rudolf Minder

  DOI：10.1080/07328309808002338

  日期：1998.5.1

  Two derivatives of beta-maltosyl-(1-->4)-trehalose monodeoxygenated at C-2 or C-2' have been synthesized in [2+2] block syntheses. N-Iodosuccinimide-mediated coupling of tetra-O-benzyl-glucose to tri-O-acetyl-D-glucal followed by O-acetylation furnished 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-alpha-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside (7), which was used as a starting material for both tetrasaccharides. For the preparation of the 2'-monodeoxygenated saccharide the deoxyiodo pyranose moiety of 7 was further elaborated by de-O-acetylation, O-benzylidenation, O-benzylation, and selective reductive opening of the benzylidene acetal to give glycosyl acceptor 10. Glycosylation with hepta-O-acetylmaltosyl bromide and deprotection including removal of the iodo substituent afforded the 2'-deoxymaltosyl-(1-->4)-trehalose 14. On the other hand, the non-iodinated pyranose moiety of 7 was transformed to a glycosyl acceptor. The removal of the benzyl groups of 7 necessitated also the reduction of the iodo group at this early stage. The resulting 3,4,6-tri-O-acetyl-2-deoxy-alpha-D-arabino-hexopyranosyl alpha-D-glucopyranoside was subjected to a similar reaction sequence as above to finally result in the 2-deoxymaltosyl-(1-->4)-trehalose 22.