[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methanol | 1428741-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methanol
• CAS: 1428741-40-5
• 化学式: C₁₆H₃₈O₆Si₃
• 分子量: 410.731
• InChiKey: VFMWHUHHZDIWSF-CWVYHPPDSA-N

物化性质

• 沸点：
  381.7±42.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methanol 、 乙酸酐 在 吡啶 作用下， 反应 2.0h， 生成 2,3,4-tri-O-trimethylsilyl-6-O-acetyl-α-D-methyl 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
• 作为产物：
  描述：

  methyl 2,3,4,6-tetrakis-O-(trimethylsilyl)-α-D-galactopyranoside 在 (O-carboxymethyl)hydroxylamine 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 [(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(trimethylsilyloxy)oxan-2-yl]methanol
  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

文献信息

• Novel eco-friendly solution for the regioselective acetylation of per-O-TMS carbohydrates
  作者：Lina Jin、Xianya Mao、Zhikun Wang、Yangyi Mao、Jianwei Mao、Yanli Cui

  DOI：10.1016/j.carres.2020.108074

  日期：2020.9

  Regioselective acetylation of per-O-TMS carbohydrates was achieved preferentially at the 6 position or 1,6-position under mild conditions involving the eco-friendly solvent acetonitrile, at room temperature, in ambient atmosphere and in a shorter time. Good or moderate yields were obtained via 4-dimethylaminopyridine, without auxiliary equipment. A single α-O-Acetyl acetylation anomer was exclusively

  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。
• Regioselective 6-detrimethylsilylation of per-O-TMS-protected carbohydrates in the presence of ammonium acetate
  作者：Yanli Cui、Zhaodong Cheng、Jianwei Mao、Yongping Yu

  DOI：10.1016/j.tetlet.2013.05.039

  日期：2013.7

  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.