n-pentyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-eno-septanoside | 1608472-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: n-pentyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-eno-septanoside
• 英文别名: n-pentyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabinohept-2-enoseptanoside；(2R,3R,4S,7S)-6-chloro-7-pentoxy-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,7-tetrahydrooxepine
• CAS: 1608472-02-1
• 化学式: C₄₀H₄₅ClO₆
• 分子量: 657.247
• InChiKey: LAATZYAECJPSBS-IRBZWDKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-pentyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-eno-septanoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到n-pentyl-2-chloro-2-deoxy-α-D-manno-sept-3-uloside
  参考文献：
  名称：

  Dense network of OH⋯O and CH⋯O interactions in the solid state structure of n-pentyl-2-chloro-2-deoxy-α-d-manno-sept 3-uloside

  摘要：

  Single crystal X-ray structural analysis of a septanoside, namely, n-pentyl-2-chloro-2-deoxy sept-3-uloside (1) provides many finer details of the molecular structure, in addition to its preferred twist-chair conformation, namely, (TC3,4)-T-5,6 conformation. Structural analysis reveals a dense network of O-H...O, C-H...O and van der Waals interactions that stabilize interdigitized, planar bi-layer structure of the crystal lattice. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.04.019
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol 在 18-冠醚-6 、 苄基三乙基氯化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 54.0h， 生成 n-pentyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-eno-septanoside
  参考文献：
  名称：

  葡糖苷中糖苷键的水解：单-，二-和2-氯-2-脱氧-庚糖苷的比较。

  摘要：

  本文报道了在酸催化下一氯，二氯和2-氯-2-脱氧Septanosides的水解稳定性的动力学研究。单糖苷和二糖苷的比较表明，二糖中的糖苷键比单糖更稳定。此外，还原端的糖苷键水解几乎是二糖非还原端的糖苷键水解速度的两倍。发现2-氯-2-脱氧庚糖苷是最稳定的，并且其糖苷键水解仅在升高的温度下发生。建议外环羟甲基的取向和诱导作用在水解速率中起作用。

  DOI：

  10.1016/j.carres.2014.05.013

文献信息

• Exclusive ring opening of gem-dihalo-1,2-cyclopropanated oxyglycal to oxepines in AgOAc
  作者：Supriya Dey、N. Jayaraman

  DOI：10.1016/j.carres.2014.01.023

  日期：2014.5

  Treatment of gem-dihalo-1,2-cyclopropanated D-oxyglycal with primary, secondary, and unsaturated alcohols, in the presence of AgOAc, leads to the formation of chloro-oxepines exclusively. Reaction of the resulting 2-chloro-oxepines with excess alcohol in the presence of AgOAc, do not promote further reactions. This result is in contrast to the reactions of D-glucal derived halo-oxepine with alcohols known previously that lead to the formation of furanoses as the major product under similar reaction conditions. Observation of this study consolidates the reactivity differences of gem-dihalo-1,2-cyclopropanated oxyglycals, as compared to gem-dihalo- 1,2-cyclopropanated glycals. (C) 2014 Elsevier Ltd. All rights reserved.