(2R,3S,4R,5R)-4,5-O-isopropylidene-1,2,3,4,5-dodecanepentol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R)-4,5-O-isopropylidene-1,2,3,4,5-dodecanepentol
• 英文别名: (1S,2R)-1-[(4S,5R)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl]propane-1,2,3-triol
• 化学式: C₁₅H₃₀O₅
• 分子量: 290.4
• InChiKey: OYSJNYDFGHFNGC-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-((4S,5R)-5-heptyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 在 四溴化碳 作用下， 以 甲醇 为溶剂， 反应 43.0h， 以72%的产率得到(2R,3S,4R,5R)-4,5-O-isopropylidene-1,2,3,4,5-dodecanepentol
  参考文献：
  名称：

  CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups

  摘要：

  CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.205

文献信息

• Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Kuo-Cheng Lu、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.09.095

  日期：2004.12

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.