1,2,3,4-tetra-O-trimethylsilyl-6-O-acetyl-D-galactopyranoside | 1242551-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4-tetra-O-trimethylsilyl-6-O-acetyl-D-galactopyranoside
• 英文别名: trimethylsilyl 6-O-acetyl-2,3,4-tris-O-trimethylsilyl-α-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis(trimethylsilyloxy)oxan-2-yl]methyl acetate
• CAS: 1242551-06-9
• 化学式: C₂₀H₄₆O₇Si₄
• 分子量: 510.923
• InChiKey: QNVIUFBMYOFYMS-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-trimethylsilyl-6-O-acetyl-D-galactopyranoside 在 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  用于新型O-TMS碳水化合物的区域选择性乙酰化的新型环保解决方案。

  摘要：

  在温和条件下，在环境友好的环境中，在室温，环境气氛中且在较短的时间内，优先在6位或1,6-位上实现per-O-TMS碳水化合物的区域选择性乙酰化。在没有辅助设备的情况下，通过4-二甲基氨基吡啶获得了良好或中等的产率。单独为涉及的底物定义了一个单一的α-O-乙酰乙酰化单体。应用6-O-单乙酸酯衍生物并将其用作二糖构建中的稳定的糖基供体。该方法学成功用于多种底物，包括：d-乳糖，d-海藻糖，d-半乳糖，甲基α-d-半乳糖，d-葡萄糖，d-甘露糖，d-木糖和l-岩藻糖。

  DOI：

  10.1016/j.carres.2020.108074
• 作为产物：
  描述：

  1,2,3,4,6-五-O-(三甲基硅烷基)alpha-D-半乳糖 在 吡啶 、 ammonium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 1,2,3,4-tetra-O-trimethylsilyl-6-O-acetyl-D-galactopyranoside
  参考文献：
  名称：

  Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate

  摘要：

  A convenient methodology has been developed for the regioselective removal of primary trimethylsilyl group (TMS) of various per-O-TMS-protected carbohydrates by inexpensive ammonium acetate. After acetylation and trichloroacetimidation of 6-hydroxyl sugar 1b, other TMS groups of 1d and 1c were inert to ammonium acetate in the same conditions, and this approach was also successfully applied in TMS-protected sphingosine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.039

文献信息

• TMSOTf-Catalyzed Silylation: Streamlined Regioselective One-Pot Protection and Acetylation of Carbohydrates
  作者：A. Abragam Joseph、Ved Prakash Verma、Xin-Yi Liu、Chia-Hui Wu、Vijay M. Dhurandhare、Cheng-Chung Wang

  DOI：10.1002/ejoc.201101267

  日期：2012.2

  A highly efficient TMSOTf-catalyzed HMDS silylation of sugars, which can easily be integrated with subsequent reactions in one-pot fashion, has been developed. Its usefulness was demonstrated by applications to streamlined regioselective one-pot protection and nonenzymatic acetylation of un

  已经开发出一种高效的 TMSOTf 催化的 HMDS 糖基硅烷化，它可以很容易地以一锅法与后续反应相结合。其在简化区域选择性一锅法保护和非酶乙酰化方面的应用证明了其有用性。
• Selective Acetylation of per-<i>O</i>-TMS-Protected Monosaccharides
  作者：Mark A. Witschi、Jacquelyn Gervay-Hague

  DOI：10.1021/ol101751d

  日期：2010.10.1

  Selective acetylation of various per-O-TMS-protected carbohydrates has been accomplished. Using a protecting group exchange strategy and microwave assistance, monosaccharides (glucose, galactose, and mannose) can be selectively acetylated producing either the 6-O-monoacetate or 1,6-O-diacetylated species. This new class of molecules can be deprotected without migration of the acetyl groups, providing useful synthetic intermediates. To demonstrate the scope of the reaction, the methodology was successfully extended to TMS-protected ceramide.