(R)-1-O-(2-trimethylsilylethyl)-6-O-[4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-2'-methylenebutanoyl]-β-D-glucopyranoside | 1055311-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (R)-1-O-(2-trimethylsilylethyl)-6-O-[4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-2'-methylenebutanoyl]-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-trimethylsilylethoxy)oxan-2-yl]methyl (3R)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-methylidenebutanoate
• CAS: 1055311-09-5
• 化学式: C₂₂H₄₄O₉Si₂
• 分子量: 508.757
• InChiKey: BGKHKSGZYKPGGV-WKOMVXTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (R)-1-O-(2-trimethylsilylethyl)-6-O-[4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-2'-methylenebutanoyl]-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以93%的产率得到epi-6-tuliposide B
  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-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

文献信息

• 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.