((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane | 616239-52-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane
• 英文别名: diethyl-(4-methoxyphenyl)-[(2R,3R,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxysilane
• CAS: 616239-52-2
• 化学式: C₄₃H₅₄O₇Si
• 分子量: 710.983
• InChiKey: WBVDAISFDXLPIS-BQLIBBPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane 在 钯 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-methoxy-4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q
• 作为产物：
  描述：

  4-pentenyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.25h， 生成 ((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q

文献信息

• Stereodirected Synthesis of Aryl α-<i>C</i>-Glycosides from 2-<i>O</i>-Arylsilyl-glucopyranosides
  作者：Cyril Rousseau、Olivier R. Martin

  DOI：10.1021/ol035529q

  日期：2003.10.1

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.