dec-9-enyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 155197-25-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dec-9-enyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: 9-decenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyanoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-dec-9-enoxyoxan-2-yl]methyl acetate
• CAS: 155197-25-4
• 化学式: C₂₄H₃₈O₁₀
• 分子量: 486.56
• InChiKey: JQODBDZWOUIDCV-DJCPXJLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  dec-9-enyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 甲醇 、 sodium methylate 作用下， 反应 1.0h， 生成 9-decenyl α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and anti-tumor activity of carbohydrate analogues of the tetrahydrofuran containing acetogenins

  摘要：

  The tetrahydrofuran (THF) containing annonaceous acetogenins (AAs) are attractive candidates for drug development because of their potent cytotoxicity against a wide range of tumors and their relatively simple and robust structures. Replacement of the THF segment with a sugar residue may deliver analogues with improved tumor selectivity and pharmacokinetics and are therefore attractive for drug development. As a first test to the feasibility of such structures, a set of such monosaccharide analogues was synthesized and assayed against four human tumor cell lines, cervical (HeLa), breast (MDA-MB231), T-cell leukemia (Jurkat) and prostate (PC-3). Certain analogues showed low micromolar activity that was comparable to a structurally similar, naturally occurring mono-THF acetogenin. A preliminary examination of the structure-activity profile of these carbohydrate analogues suggests that they have a similar mechanism of action as their THF congeners. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.027
• 作为产物：
  描述：

  (3aS,5R,6R,7S,7aS)-5-(acetoxymethyl)-2-(dec-9-en-1-yloxy)-2-methyltetrahydro-5H-[1,3]dioxolo[4,5-b]pyran-6,7-diyl diacetate 在 zinc(II) iodide 作用下， 反应 21.0h， 以80%的产率得到dec-9-enyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides

  摘要：

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.032

文献信息

• Nikolaev, Andrey V.; Rutherford, Trevor J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1977 - 1988
  作者：Nikolaev, Andrey V.、Rutherford, Trevor J.、Ferguson, Michael A. J.、Brimacombe, John S.

  DOI：——

  日期：——