p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-xylo-hex-3-ulopyranoside | 1001847-00-2

• 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-benzylidene-2-O-tris(isopropyl)silyl-β-D-xylo-hex-3-ulopyranoside
• 英文别名: (2S,4aR,6S,7S,8aS)-6-(4-methoxyphenoxy)-2-phenyl-7-tri(propan-2-yl)silyloxy-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-one
• CAS: 1001847-00-2
• 化学式: C₂₉H₄₀O₇Si
• 分子量: 528.718
• InChiKey: KWJFZJNHZVVFHS-YJWDFKAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-xylo-hex-3-ulopyranoside 、 二溴二氟甲烷 在 三(二甲胺基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以76%的产率得到p-methoxyphenyl 4,6-O-benzylidene-3-deoxy-3-C-(difluoromethylene)-2-O-tris(isopropyl)silyl-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
• 作为产物：
  描述：

  p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-β-D-galactopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 反应 10.5h， 以93%的产率得到p-methoxyphenyl 4,6-O-benzylidene-2-O-tris(isopropyl)silyl-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

• Reactions of Carbonyl Compounds with Phosphorus Ylide Generated from Tribromofluoromethane and Tris(dimethylamino)phosphine
  作者：Go Hirai、Eri Nishizawa、Daiki Kakumoto、Masaki Morita、Mitsuaki Okada、Daisuke Hashizume、Sayoko Nagashima、Mikiko Sodeoka

  DOI：10.1246/cl.150523

  日期：2015.10.5

  The reactions of fluorinated ylide, generated from tris(dimethylamino)phosphine and tribromofluoromethane, with simple aldehydes and reactive ketones gave the expected Wittig reaction products. How...

  由三（二甲氨基）膦和三溴氟甲烷生成的氟化叶立德与简单的醛和反应性酮反应得到预期的 Wittig 反应产物。如何...
• Synthesis of <i>CH₂</i>-Linked α(2,3)Sialylgalactose Analogue: On the Stereoselectivity of the Key Ireland-Claisen Rearrangement
  作者：Toru Watanabe、Go Hirai、Marie Kato、Daisuke Hashizume、Taeko Miyagi、Mikiko Sodeoka

  DOI：10.1021/ol801519j

  日期：2008.10.2

  -linked alpha(2,3)sialylgalactose analogue was efficiently synthesized using an Ireland-Claisen rearrangement, which was developed recently by our group for constructing a CF 2 -sialoside. The reaction conditions of the rearrangement were optimized for alpha-stereoselective formation of the CH 2 -sialoside. On the basis of the observed temperature effects, the origin of the stereoselectivity of the Ireland-Claisen

  CH 2连接的alpha（2,3）唾液酸半乳糖类似物是使用Ireland-Claisen重排有效合成的，该重排最近由我们小组开发，用于构建CF 2-唾液苷。对于CH 2-唾液酸的α-立体选择性形成，对重排的反应条件进行了优化。基于观察到的温度效应，讨论了爱尔兰-克莱森重排的立体选择性的起源。此外，借助于立体选择性二羟基化和脱氧，实现了重排产物的半乳糖单元上的2α-羟基的重建。
• 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.