acetyl 5-O-acetyl-3-O-tert-butyl(dimethyl)silyl-2-O-(1-acetoxy-1-methylethyl)β-D-xylofuranoside | 1202373-37-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetyl 5-O-acetyl-3-O-tert-butyl(dimethyl)silyl-2-O-(1-acetoxy-1-methylethyl)β-D-xylofuranoside
• 英文别名: 2-O-(2-acetoxyisopropyl)-1,5-di-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-xylofuranoside；[(2R,3S,4R,5S)-5-acetyloxy-4-(2-acetyloxypropan-2-yloxy)-3-[tert-butyl(dimethyl)silyl]oxyoxolan-2-yl]methyl acetate
• CAS: 1202373-37-2
• 化学式: C₂₀H₃₆O₉Si
• 分子量: 448.586
• InChiKey: UMAHXFICFNZOEP-XMTFNYHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酸酐 、 [(3aR,5R,6S,6aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-dimethylsilane 在 高氯酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以84%的产率得到acetyl 5-O-acetyl-3-O-tert-butyl(dimethyl)silyl-2-O-(1-acetoxy-1-methylethyl)β-D-xylofuranoside
  参考文献：
  名称：

  A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4–SiO2

  摘要：

  The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO4-SiO2 under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl beta-D-furanosides with a 2-acetoxyisopropyl group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.08.035

文献信息

• An atom-efficient and powerful method for direct esterification of silyl ethers catalyzed by HClO4–SiO2
  作者：Ti-Jian Du、Qin-Pei Wu、Hai-Xia Liu、Xi Chen、Yi-Nan Shu、Xiao-Dong Xi、Qing-Shan Zhang、Yun-Zheng Li

  DOI：10.1016/j.tet.2010.12.028

  日期：2011.2

  An efficient and convenient procedure for direct esterification of alkyl and aryl silyl ethers with Ac2O and a catalyst system of perchloric acid immobilized on a silica gel (HClO4 SiO2) has been developed. The silyl protecting groups are directly replaced by acetyls and the protecting groups themselves are transformed into acetates as the sole byproducts, which can be readily recovered and converted back to silylchlorides, the original protecting agents, thus minimizing wastes. (C) 2010 Elsevier Ltd. All rights reserved.