methyl (2R,4S,5R,6R)-2-[[(2S,4aR,6S,8aR)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]-difluoromethyl]-5-acetamido-4-(phenylmethoxymethoxy)-6-[(1S,2R)-1,2,3-tris(phenylmethoxymethoxy)propyl]oxane-2-carboxylate | 1001847-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,4S,5R,6R)-2-[[(2S,4aR,6S,8aR)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]-difluoromethyl]-5-acetamido-4-(phenylmethoxymethoxy)-6-[(1S,2R)-1,2,3-tris(phenylmethoxymethoxy)propyl]oxane-2-carboxylate
• CAS: 1001847-05-7
• 化学式: C₆₆H₇₃F₂NO₁₈
• 分子量: 1206.3
• InChiKey: UWYMAZNRKLZLLR-RJMDKQSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  87
• 可旋转键数：
  33
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  194
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S,5R,6R)-2-[[(2S,4aR,6S,8aR)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]-difluoromethyl]-5-acetamido-4-(phenylmethoxymethoxy)-6-[(1S,2R)-1,2,3-tris(phenylmethoxymethoxy)propyl]oxane-2-carboxylate 在 溶剂黄146 作用下， 反应 2.0h， 以80%的产率得到
  参考文献：
  名称：

  Stereocontrolled and Convergent Entry to CF₂-Sialosides:  Synthesis of CF₂-Linked Ganglioside GM4

  摘要：

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

  DOI：

  10.1021/ja075738w
• 作为产物：
  描述：

  [(2S,4aR,6S,7R,8aR)-8-(difluoromethylidene)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-7-yl] (2S,4S,5R,6R)-5-acetamido-4-(phenylmethoxymethoxy)-6-[(1S,2R)-1,2,3-tris(phenylmethoxymethoxy)propyl]oxane-2-carboxylate 、 三甲基硅烷化重氮甲烷 在 三甲基氯硅烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 1.5h， 以86%的产率得到methyl (2R,4S,5R,6R)-2-[[(2S,4aR,6S,8aR)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl]-difluoromethyl]-5-acetamido-4-(phenylmethoxymethoxy)-6-[(1S,2R)-1,2,3-tris(phenylmethoxymethoxy)propyl]oxane-2-carboxylate
  参考文献：
  名称：

  Stereocontrolled and Convergent Entry to CF₂-Sialosides:  Synthesis of CF₂-Linked Ganglioside GM4

  摘要：

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.

  DOI：

  10.1021/ja075738w

文献信息

• Stereocontrolled and Convergent Entry to <i>CF</i><i>₂</i>-Sialosides:  Synthesis of <i>CF</i><i>₂</i>-Linked Ganglioside GM4
  作者：Go Hirai、Toru Watanabe、Kazunori Yamaguchi、Taeko Miyagi、Mikiko Sodeoka

  DOI：10.1021/ja075738w

  日期：2007.12.1

  Sialidase-resistant ganglioside analogues having biological activities similar to those of natural gangliosides are expected to be important probes for clarifying the biological functions of gangliosides. Focusing on difluoromethylene-linked (CF2-linked) alpha(2,3) sialylgalactose as a core structure of sialidase-resistant ganglioside mimics, we have developed novel, stereocontrolled, and efficient methodologies to synthesize CF2-sialosides based on Ireland-Claisen rearrangement. CF2-linked alpha(2,3)sialylgalactose and CF2-linked GM4 were synthesized.