(1S)-1,5-anhydro-1-C-phenyl-D-mannitol | 882302-28-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1,5-anhydro-1-C-phenyl-D-mannitol
• 英文别名: (1S)-1-phenyl-1,5-anhydro-D-mannitol；(1S)-1-Phenyl-1,5-anhydro-D-mannit；(2R,3S,4R,5S,6S)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-3,4,5-triol；(2R,3S,4R,5S,6S)-2-(hydroxymethyl)-6-phenyloxane-3,4,5-triol
• CAS: 882302-28-5
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: NOFZOJZALFHRLE-GCHJQGSQSA-N

物化性质

• 熔点：
  206-207 °C
• 沸点：
  466.7±45.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 (1S)-1,5-anhydro-1-C-phenyl-D-mannitol 在 吡啶 作用下， 反应 24.0h， 以74%的产率得到(2S,3S,4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-2-phenyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol
  参考文献：
  名称：

  Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals

  摘要：

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.048
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 甲醇 、 sodium methylate 作用下， 生成 (1S)-1,5-anhydro-1-C-phenyl-D-mannitol
  参考文献：
  名称：

  Reactions of Polyacylglycosyl Halides with Grignard Reagents

  摘要：

  DOI：

  10.1021/ja01160a087

文献信息

• Regioselective Deacetylation of Peracetylated Deoxy-<i>C</i>-glycopyranosides by Boron Trichloride (BCl₃)
  作者：Shuangyuan Chen、Feifei Wei、Xinqiang Cheng、Ying Luo、Fancui Meng、Yuanwen Zhang、Wenqian Huang、Jun Lv、Hong Pan、Qingqing Wu、Guilong Zhao

  DOI：10.1021/acs.joc.4c00026

  日期：2024.4.5

  for regioselective deacetylation at sugar 3-OH of peracetylated 6-deoxy-C-glucopyranosides mediated by BCl3 was developed. The approach could be extended to other sugar-derived 6-deoxy-C-glycopyranosides, such as those derived from mannose, galactose, and rhamnose, with deacetylation occurring at varied sugar hydroxyl groups, and further extended to 4-deoxy-C-glucopyranosides with deacetylation occurring

  开发了由 BCl 3介导的全乙酰化 6-脱氧-C-吡喃葡萄糖苷的糖 3-OH 区域选择性脱乙酰化的通用方法。该方法可以扩展到其他糖衍生的 6-脱氧-C-吡喃葡萄糖苷，例如衍生自甘露糖、半乳糖和鼠李糖的那些，在不同的糖羟基上发生脱乙酰化，并进一步扩展到 4-脱氧-C-吡喃葡萄糖苷糖3-OH处发生脱乙酰化。该方法将能够获得具有合成挑战性的碳水化合物衍生物。提出了区域选择性的可能机制。
• Reactions of Polyacylglycosyl Halides with Grignard Reagents
  作者：Charles D. Hurd、Roman P. Holysz

  DOI：10.1021/ja01160a087

  日期：1950.4
• Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals
  作者：Steven Van Hoof、Bart Ruttens、Idzi Hubrecht、Gert Smans、Petra Blom、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove、Johan Van der Eycken

  DOI：10.1016/j.bmcl.2005.12.048

  日期：2006.3

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.