[(2R,3S,4S,5R,6S)-6-[(3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy-tert-butyl-diphenylsilane | 1030376-70-5

• 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-[(3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 1030376-70-5
• 化学式: C₇₀H₇₆O₁₀Si
• 分子量: 1105.45
• InChiKey: JGTPQJWYCIMWBG-LQUOZWNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.22
• 重原子数：
  81
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-6-[(3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy-tert-butyl-diphenylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到[(2R,3S,4S,5R,6R)-6-[(3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
  参考文献：
  名称：

  Structural establishment of polygalatenosides A and B by total synthesis

  摘要：

  The first total synthesis of polygalatenosides A (1) and B (2), originally isolated from the traditional Chinese medicine and reported as antidepressant agents, is described here. Glycosylation between thiogalactosyl donors 6 and 7 and 1-deoxyglucosyl acceptor 5 yielded the corresponding key intermediates 10 and 16, respectively, with an alpha(1 -> 2)-glycosidic linkage in moderate yields. In addition, D-configuration of the galactoside residue in 1 and 2 was confirmed in our studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.032
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-6-O-(tert-butyl)diphenylsilyl-1-thio-β-D-galactopyranoside 、 1-deoxy-3,4,6-tri-O-benzyl-D-glucopyranose 在 N-碘代丁二酰亚胺 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到[(2R,3S,4S,5R,6S)-6-[(3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy-tert-butyl-diphenylsilane
  参考文献：
  名称：

  Structural establishment of polygalatenosides A and B by total synthesis

  摘要：

  The first total synthesis of polygalatenosides A (1) and B (2), originally isolated from the traditional Chinese medicine and reported as antidepressant agents, is described here. Glycosylation between thiogalactosyl donors 6 and 7 and 1-deoxyglucosyl acceptor 5 yielded the corresponding key intermediates 10 and 16, respectively, with an alpha(1 -> 2)-glycosidic linkage in moderate yields. In addition, D-configuration of the galactoside residue in 1 and 2 was confirmed in our studies. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.03.032

文献信息

• Structural establishment of polygalatenosides A and B by total synthesis
  作者：Chih-Ming Huang、Rai-Shung Liu、Tian-Shung Wu、Wei-Chieh Cheng

  DOI：10.1016/j.tetlet.2008.03.032

  日期：2008.4

  The first total synthesis of polygalatenosides A (1) and B (2), originally isolated from the traditional Chinese medicine and reported as antidepressant agents, is described here. Glycosylation between thiogalactosyl donors 6 and 7 and 1-deoxyglucosyl acceptor 5 yielded the corresponding key intermediates 10 and 16, respectively, with an alpha(1 -> 2)-glycosidic linkage in moderate yields. In addition, D-configuration of the galactoside residue in 1 and 2 was confirmed in our studies. (c) 2008 Elsevier Ltd. All rights reserved.