benzyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside | 1608472-11-2

• 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: benzyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside
• 英文别名: (2R,3R,4S,7S)-6-chloro-3,4,5,7-tetrakis(phenylmethoxy)-2-(phenylmethoxymethyl)-2,3,4,7-tetrahydrooxepine
• CAS: 1608472-11-2
• 化学式: C₄₂H₄₁ClO₆
• 分子量: 677.237
• InChiKey: YQXAUBODAOVRMZ-SDPSVZJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl 1,5-anhydro-D-arabino-hex-1-enitol 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 78.0h， 生成 benzyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabino-hept-2-enoseptanoside 、 acetyl 2-chloro-2-deoxy-3,4,5,7-tetra-O-benzyl-α-D-arabinohept-2-enoseptanoside
  参考文献：
  名称：

  Exclusive ring opening of gem-dihalo-1,2-cyclopropanated oxyglycal to oxepines in AgOAc

  摘要：

  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.

  DOI：

  10.1016/j.carres.2014.01.023

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.