ethyl 6-O-tert-butyldimethylsilyl-2-thio-β-D-fructofuranoside | 302905-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-tert-butyldimethylsilyl-2-thio-β-D-fructofuranoside
• CAS: 302905-18-6
• 化学式: C₁₄H₃₀O₅SSi
• 分子量: 338.541
• InChiKey: XXEDAKXFUJSEFN-NMKXLXIOSA-N

物化性质

• 熔点：
  61-62 °C(Solv: heptane (142-82-5))
• 沸点：
  434.6±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-tert-butyldimethylsilyl-2-thio-β-D-fructofuranoside 在 吡啶 、 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 sodium hydroxide 、 di-tert-butylmethylpyridine 、 四丁基硫酸氢铵 、 DMTST 、 tris(dimethylamino)sulfonium trimethylsilyldifluoride 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 132.0h， 生成 2,3,3',4,6-penta-O-benzylsucrose
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 ethyl 2-thio-β-D-fructofuranoside 在 吡啶 作用下， 以76%的产率得到ethyl 6-O-tert-butyldimethylsilyl-2-thio-β-D-fructofuranoside
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u

文献信息

• Hydrogen-Bond-Mediated Aglycone Delivery: Synthesis of β-<scp>d</scp>-Fructofuranosides
  作者：Pan Wang、Yidian Mo、Xiaoyu Cui、Xuyang Ding、Xiao Zhang、Zhongjun Li

  DOI：10.1021/acs.orglett.0c00702

  日期：2020.4.17

  work, we developed an efficient method for the synthesis of β-d-fructofuranosides by using a 6-picoloyl-protected fructofuranosyl thioglycoside as the glycosyl donor. Subsequently, we applied the approach to a wide variety of donors and acceptors. Furthermore, the successful synthesis of levantetrose confirmed its applicability in the multistep synthesis of oligosaccharides.

  β- d-果糖呋喃糖苷键的构建是碳水化合物化学中的主要挑战之一。在这项工作中，我们开发了用于β-的合成的有效方法d通过使用6 picoloyl保护的果糖基硫代糖苷作为糖基供体-fructofuranosides。随后，我们将该方法应用于各种捐赠者和接受者。此外，Levantetrose的成功合成证实了其在寡糖的多步合成中的适用性。