p-methoxyphenyl 4,6-O-p-methoxyphenylbenzylidene-3-deoxy-3-C-(difluoromethylene)-β-D-xylo-hex-3-ulopyranoside | 1001847-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: p-methoxyphenyl 4,6-O-p-methoxyphenylbenzylidene-3-deoxy-3-C-(difluoromethylene)-β-D-xylo-hex-3-ulopyranoside
• 英文别名: (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-ol
• CAS: 1001847-02-4
• 化学式: C₂₂H₂₂F₂O₇
• 分子量: 436.409
• InChiKey: UCMZYLOPTRJBDG-JTIOYYDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  9

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	[(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	1001847-03-5	C65H71F2NO18	1192.27

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-O-p-methoxyphenylbenzylidene-3-deoxy-3-C-(difluoromethylene)-β-D-xylo-hex-3-ulopyranoside 、 N-acetyl-4,7,8,9-tetra-O-benzyloxymethyl-2-deoxy-neuraminic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到[(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
  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-(difluoromethylene)-6-(4-methoxyphenoxy)-2-(4-methoxyphenyl)hexahydropyrano[3,2-d][1,3]dioxin-7-yl)oxy)triisopropylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以7.5 g的产率得到p-methoxyphenyl 4,6-O-p-methoxyphenylbenzylidene-3-deoxy-3-C-(difluoromethylene)-β-D-xylo-hex-3-ulopyranoside
  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.