2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-1,2-O-[8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctan-1-yloxyethylidene]-β-D-manno-heptopyranose | 540501-09-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-1,2-O-[8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctan-1-yloxyethylidene]-β-D-manno-heptopyranose
• CAS: 540501-09-5
• 化学式: C₄₆H₇₅BrO₁₁
• 分子量: 883.999
• InChiKey: FLUJBUGIXBZJIH-LMJTXECWSA-N

物化性质

• 沸点：
  798.5±60.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  58.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  117.21
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-1,2-O-[8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctan-1-yloxyethylidene]-β-D-manno-heptopyranose 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 16.08h， 生成
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 2,4,6-三甲基吡啶 、 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 硫酸 、 氢溴酸 、 氢气 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 lithium bromide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 、 丁酮 为溶剂， 反应 63.58h， 生成 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-1,2-O-[8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctan-1-yloxyethylidene]-β-D-manno-heptopyranose
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297

文献信息

• A convenient synthetic route to mannose 6-phosphonate-cholesteryl conjugate
  作者：Sébastien Vidal、Alain Morère、Jean-Louis Montero

  DOI：10.1002/hc.10134

  日期：——

  is described involving (1) a one-carbon chain elongation at the 6-position of mannose, followed by (2) phosphonation, using tris(trimethylsilyl)phosphite. This method was shown to e efficient and provides a general route to various mannose 6-phosphonate-based compounds for the design of drug delivery systems. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:241–246, 2003; Published online in Wiley

  描述了基于甘露糖 6-膦酸酯的糖脂的多步合成，包括 (1) 在甘露糖的 6 位进行单碳链延长，然后 (2) 使用亚磷酸三(三甲基甲硅烷基)酯进行磷酸化。该方法被证明是有效的，并为设计药物递送系统的各种基于甘露糖 6-膦酸酯的化合物提供了通用途径。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:241–246, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10134