(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran | 173325-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
• CAS: 173325-22-9
• 化学式: C₆₁H₆₃ClO₁₀
• 分子量: 991.618
• InChiKey: XQMVDPAOFQLNCX-ZBNUIHJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.42
• 重原子数：
  72.0
• 可旋转键数：
  25.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

  摘要：

  Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

  DOI：

  10.1021/jo901945e
• 作为产物：
  描述：

  1-O-acetyl-2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-D-glucopyranose 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Uchida, Chikara; Kitahashi, Hideo; Watanabe, Shinsuke, Journal of the Chemical Society. Perkin transactions I, 1995, # 13, p. 1707 - 1718

  摘要：

  DOI：

文献信息

• Synthesis and biological activities of NB-506 analogues modified at the glucose group
  作者：Mitsuru Ohkubo、Teruyuki Nishimura、Hiroshi Kawamoto、Masato Nakano、Teruki Honma、Tomoko Yoshinari、Hiroharu Arakawa、Hiroyuki Suda、Hajime Morishima、Susumu Nishimura

  DOI：10.1016/s0960-894x(00)00004-4

  日期：2000.3

  A new indolocarbazole compound, NB-506 (1), modified at the glucose group yielded a beta-D-glucopyranoside, J-107,088 (2), which showed potent anticancer activity. A beta-D-ribofuranoside, J-109,534 (3), was found to be 6 times more potent than J-107,088 at inhibiting topoisomerase I.

  在葡萄糖基团上修饰的新吲哚并咔唑化合物NB-506（1）产生了β-D-吡喃葡萄糖苷J-107,088（2），该化合物具有强大的抗癌活性。发现β-D-核呋喃糖苷J-109,534（3）在抑制拓扑异构酶I方面的效力是J-107,088的6倍。
• Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety
  作者：Fabio Animati、Marco Berettoni、Mario Bigioni、Monica Binaschi、Amalia Cipollone、Clelia Irrissuto、Federica Nardelli、Lauso Olivieri

  DOI：10.1016/j.bmcl.2012.06.016

  日期：2012.8

  rebeccamycin represent an important class of antitumour drugs. In the course of our structure–activity relationship studies, new rebeccamycin analogues modified at the imide moiety were synthesised. The antiproliferative activity of the compounds was evaluated on three human cancer cell lines, A2780 (ovarian cancer), H460 (lung cancer), and GLC4 (small-cell lung cancer). The in vitro cytotoxicity of

  与抗生素瑞贝卡霉素相关的糖基化吲哚并咔唑代表了一类重要的抗肿瘤药物。在我们的结构-活性关系研究过程中，合成了在酰亚胺部分修饰的新的瑞贝卡霉素类似物。在三种人类癌细胞系A2780（卵巢癌），H460（肺癌）和GLC4（小细胞肺癌）中评估了化合物的抗增殖活性。化合物2和4的体外细胞毒性分别以与酰亚胺部分相连的1,3-二氧戊环和（1,3-二氧杂环-4-基）亚甲基为特征，高于参考化合物依地卡林。还研究了化合物2在A2780异种移植模型中诱导肿瘤消退的作用。