6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-D-glucopyranoside | 1055311-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl prop-2-enoate
• CAS: 1055311-17-5
• 化学式: C₁₄H₂₆O₇Si
• 分子量: 334.442
• InChiKey: WAKDMSFKLCNKKW-RGCYKPLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-D-glucopyranoside 、 叔丁基二甲基硅氧烷基乙醛 在 3-hydroxy quinuclidine 作用下， 以 二甲基亚砜 为溶剂， 反应 40.0h， 生成 (R)-1-O-(2-trimethylsilylethyl)-6-O-[4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-2'-methylenebutanoyl]-β-D-glucopyranoside 、 (S)-1-O-(2-trimethylsilylethyl)-6-O-[4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-2'-methylenebutanoyl]-β-D-glucopyranoside
  参考文献：
  名称：

  First total synthesis of 6-tuliposide B

  摘要：

  Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from D-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-beta-D-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.019
• 作为产物：
  描述：

  6-O-acryloyl-2,3,4-tri-O-trimethylsilyl-1-O-(2-trimethylsilylethyl)-β-D-glucopyranoside 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 1.17h， 以100%的产率得到6-O-acryloyl-1-O-(2-trimethylsilylethyl)-β-D-glucopyranoside
  参考文献：
  名称：

  First total synthesis of 6-tuliposide B

  摘要：

  Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from D-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-beta-D-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.019

文献信息

• The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure–activity relationship
  作者：Kengo Shigetomi、Kazuaki Shoji、Shinya Mitsuhashi、Makoto Ubukata

  DOI：10.1016/j.phytochem.2009.10.008

  日期：2010.2

  6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacteria) MurA is one of the major molecular targets of 6-tuliposide B. (C) 2009 Elsevier Ltd. All rights reserved.
• First total synthesis of 6-tuliposide B
  作者：Kengo Shigetomi、Takao Kishimoto、Kazuaki Shoji、Makoto Ubukata

  DOI：10.1016/j.tetasy.2008.05.019

  日期：2008.6

  Labile (+)-6-tuliposide B, an antimicrobial compound produced by tulip, was synthesized in nine steps from D-glucose via the Baylis-Hillman reaction of 2-(tert-butyldimethylsilyloxy)-acetaldehyde with 6-O-acryloyl-1-O-(2-trimethylsilylethyl)-beta-D-glucopyranoside, followed by a mild deprotection procedure using TFA in CH2Cl2. (C) 2008 Elsevier Ltd. All rights reserved.