2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol | 320576-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol
• 英文别名: (2S,3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-propyloxan-3-ol
• CAS: 320576-39-4
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: JFZVXMDRNLSHKJ-PGVCKJCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol 在 乙酸酐 、 二甲基亚砜 作用下， 生成 (2S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-propyloxan-3-one
  参考文献：
  名称：

  Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells

  摘要：

  A large series of alkyl C-glycosides was synthesized from D-glucal or D-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-galacto- or C-mannopyranosides, exhibited inhibitory concentrations (IC50 values) below 20 mu M, five of them in the range 4-8 mu M. Preliminary structure-activity relationships were established. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.079
• 作为产物：
  描述：

  3-(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1-propene 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以75%的产率得到2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol
  参考文献：
  名称：

  二异丁基氢化铝（DIBAL-H）作为分子手术刀：螺环重排的新机制

  摘要：

  利用我们对DIBAL-H脱O-烷基化能力的认识，我们提出了E.Suàrez所描述的螺环重排的另一种机制。我们还表明，该提议可以解释次级产品的形成，我们建议更正其原始结构。

  DOI：

  10.1016/j.tetlet.2004.09.030

文献信息

• New insights into the conformational properties of α-C-glucosides
  作者：Carlos Mayato、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.tetasy.2007.11.002

  日期：2007.11

  A series of alkyl α-d-C-glucopyranosides were synthesized and their conformational properties analyzed by CD and NMR spectroscopy. The conformational analysis revealed that the hydroxymethyl group populations (torsion angle ω, O1–C1–C2–O2) and those around the C-glucopyranosidic bond (torsion angle Φ; O2–C6–C7–C8) depend on the structural nature of the C-aglycon. The gt and the exo–syn populations

  合成了一系列烷基α-d- C-吡喃葡萄糖苷，并通过CD和NMR光谱分析了它们的构象性质。构象分析表明，羟甲基基团（扭转角ω，O1-C1-C2-O2）和C-吡喃葡萄糖苷键周围的分子（扭转角Φ； O2-C6-C7-C8）取决于分子的结构性质。C-糖苷配基。在GT和外-顺式种群增加作为Ç -aglycon变得更加取代。这些旋转种群和质子化学位移与塔夫脱的空间参数之间的线性相关性揭示了碳的重要作用C-葡糖苷的整体构象中的β-糖苷配基。随着运动的空间位阻的增加，影响羟甲基旋转的立体电子外-脱氧异头作用变得更加重要。甲伪还进行端基异构体的旋转比较研究。
• Antiproliferation and apoptosis induced by C-glycosides in human leukemia cancer cells
  作者：Carlos A. Sanhueza、Carlos Mayato、María García-Chicano、Raquel Díaz-Peñate、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2006.05.079

  日期：2006.8

  A large series of alkyl C-glycosides was synthesized from D-glucal or D-galactal. These compounds were screened against the human promyelocytic leukemia cell line (HL60), showing significant activity and apoptosis. Up to 13 C-glucopyranosides, but no C-galacto- or C-mannopyranosides, exhibited inhibitory concentrations (IC50 values) below 20 mu M, five of them in the range 4-8 mu M. Preliminary structure-activity relationships were established. (c) 2006 Elsevier Ltd. All rights reserved.
• Rearrangement of Spiroacetals of the 1,6-Dioxaspiro[4.5]decan-10-yl Methanesulfonate Type. Synthesis of Cis-Fused 1,6-Dioxadecalins
  作者：Carmen Betancor、Rosa L. Dorta、Raimundo Freire、Thierry Prangé、Ernesto Suárez

  DOI：10.1021/jo005593a

  日期：2000.12.1
• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.
• Diisobutylaluminium hydride (DIBAL-H) as a molecular scalpel: a new mechanistic proposal for a spiroketal rearrangement
  作者：Xiangbao Meng、Yongmin Zhang、Matthieu Sollogoub、Pierre Sinaÿ

  DOI：10.1016/j.tetlet.2004.09.030

  日期：2004.10

  Taking advantage of our knowledge of the capacity of DIBAL-H to de-O-alkylate, we propose an alternative mechanism for a spiroketal rearrangement described by E. Suàrez. We also show that this proposal can account for the formation of the secondary product, whose original structure we propose to correct.

  利用我们对DIBAL-H脱O-烷基化能力的认识，我们提出了E.Suàrez所描述的螺环重排的另一种机制。我们还表明，该提议可以解释次级产品的形成，我们建议更正其原始结构。