2,6-anhydro-1,3-dideoxy-4,5,7-tri-O-benzyl-D-glucohept-1-enitol | 1312437-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-anhydro-1,3-dideoxy-4,5,7-tri-O-benzyl-D-glucohept-1-enitol
• 英文别名: (2R,3S,4R)-6-methylidene-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 1312437-71-0
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: BTAXCDFJMGWYEI-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,3-dideoxy-4,5,7-tri-O-benzyl-D-glucohept-1-enitol 在 potassium osmate(VI) dihydrate 、 水 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 叔丁醇 为溶剂， 反应 72.0h， 以90%的产率得到3-deoxy-4,5,7-tri-O-benzyl-α-D-glycero-D-xylo-hept-2-ulopyranose
  参考文献：
  名称：

  Highly Efficient Synthesis of Ketoheptoses

  摘要：

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

  DOI：

  10.1021/ol2012764
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 66.0h， 生成 2,6-anhydro-1,3-dideoxy-4,5,7-tri-O-benzyl-D-glucohept-1-enitol
  参考文献：
  名称：

  Highly Efficient Synthesis of Ketoheptoses

  摘要：

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

  DOI：

  10.1021/ol2012764

文献信息

• Synthesis of Fluorinated Ketoheptoses as Specific Diagnostic Agents
  作者：Daniel Waschke、Yevgeniy Leshch、Julian Thimm、Uwe Himmelreich、Joachim Thiem

  DOI：10.1002/ejoc.201101238

  日期：2012.2

  The straightforward syntheses of six regioisomeric mono- and difluorinated D-manno-heptulose and Kamusol analogues, which use electrophilic or nucleophilic fluorinaton, are reported. D-manno-Heptulose shows attractive pharmacological properties in vivo, such as antitumour activity, as well as binding to and accumulating in pancreatic beta cells to induce hyperglycemia. The synthesised analogues represent

  报道了使用亲电或亲核氟化的六种区域异构体单和二氟化 D-甘露庚酮糖和 Kamusol 类似物的直接合成。D-甘露-庚酮糖在体内显示出有吸引力的药理学特性，例如抗肿瘤活性，以及​​与胰腺β细胞结合并在其中积累以诱导高血糖。合成的类似物代表了通过 19F MRI 技术检测和量化体内 β 细胞的有希望的探针，这有助于研究疾病进展。此外，它们是抑制肿瘤生长的潜在候选物。
• Highly Efficient Synthesis of Ketoheptoses
  作者：Daniel Waschke、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol2012764

  日期：2011.7.15

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.