[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl benzoate | 1269658-25-4

• 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,6S)-3,4,5-trihydroxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl benzoate
• CAS: 1269658-25-4
• 化学式: C₂₀H₂₂O₆S
• 分子量: 390.457
• InChiKey: FONUJTFEVIRTQT-QTVCLEQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl benzoate 在 甲醇 、 molybdenum(VI) oxychloride 作用下， 反应 66.0h， 以88%的产率得到[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methylphenyl)sulfanyloxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Chemoselective deacylation of functionalized esters catalyzed by dioxomolybdenum dichloride

  摘要：

  Among five different oxidometallic species and two Lewis acids investigated, MoO(2)Cl(2) shows the best catalytic and chemoselective activity for the deacylation of esters in methanol at ambient or elevated temperature. Both high efficiency and chemoselectivity were achieved for substrates bearing different ether or ester groups. Acylated mono and disaccharides can also be selectively deacetylated in good yields, leading to useful carbohydrate templates for further synthetic manipulations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.024

文献信息

• Flexibility in a Molecular Crystal Accomplished by Structural Modulation of Carbohydrate Epimers
  作者：Manas K. Panda、Kumar Bhaskar Pal、Gijo Raj、Rajesh Jana、Taro Moriwaki、Goutam Dev Mukherjee、Balaram Mukhopadhyay、Panče Naumov

  DOI：10.1021/acs.cgd.6b01749

  日期：2017.4.5

  bending of organic crystals is a well-known, yet mechanistically poorly understood phenomenon. On three structurally related epimers, derivatives of galactose, glucose, and mannose, it is demonstrated here that small changes in the molecular structure can have a profound effect on the mechanical properties. While the galactose derivative affords crystals which can be easily bent, the crystals of the derivatives

  有机晶体的塑性弯曲是众所周知的，但是在机械上却很少了解。在三种结构相关的差向异构体（半乳糖，葡萄糖和甘露糖的衍生物）上，这里证明了分子结构的微小变化会对机械性能产生深远的影响。虽然半乳糖衍生物提供了容易弯曲的晶体，但是葡萄糖和甘露糖的衍生物的晶体是脆性的并且不会弯曲。提供的结构，微观和机械证据表明，水分子的氢键键合是在晶体的滑动面上滑动并导致塑性弯曲的关键因素。