allyl-2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranoside | 225376-18-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: allyl-2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-2-prop-2-enoxy-6-(trityloxymethyl)oxane
• CAS: 225376-18-1
• 化学式: C₄₉H₄₈O₆
• 分子量: 732.917
• InChiKey: NYOCGJJOCSPOHR-UHKSOEAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl-2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 tert-Butyl-dimethyl-((2S,3R,4R,5R)-2,3,4,5-tetrakis-benzyloxy-6-trityloxy-hexyloxy)-silane
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i
• 作为产物：
  描述：

  氯化苄 、 1-O-allyl-6-O-trityl-β-D-glucopyranoside 在 sodium hydroxide 作用下， 反应 36.0h， 以87%的产率得到allyl-2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranoside
  参考文献：
  名称：

  Formal Synthesis of d-myo-Inositol 1,4,5-Tris(dihydrogen phosphate):  Cyclization by an Unusual Ene Reaction and Use of the Bu₂SnCl₂/Bu₂SnH₂ Reagent for Generating an Equatorial Alcohol

  摘要：

  D-Glucose was converted into the propargyl silane aldehyde 5, which, on treatment with camphorsulfonic acid, cyclized with retention of silicon. The allenic product (7) was elaborated via ketone 24 into 4, which had previously been converted into D-myo-inositol 1,4,5-tris(dihydrogen phosphate). Selective reduction of the advanced intermediate 24 was accomplished with Bu2SnCl2/Bu2SnH2, a reagent mixture that shows a very strong preference for generating equatorial alcohols. The cyclization step leading to allene 7 was studied by examining a number of model compounds; the unusual retention of silicon appears to be limited to highly oxygenated substrates, such as 5 and its all-benzyl analogue (27).

  DOI：

  10.1021/jo990086i

文献信息

• Probing myo-inositol 1-phosphate synthase with multisubstrate adducts
  作者：Rania M. Deranieh、Miriam L. Greenberg、Pierre-B. Le Calvez、Maura C. Mooney、Marie E. Migaud

  DOI：10.1039/c2ob26577j

  日期：——

  The synthesis of a series of carbohydrate–nucleotide hybrids, designed to be multisubstrate adducts mimicking myo-inositol 1-phosphate synthase first oxidative transition state, is reported. Their ability to inhibit the synthase has been assessed and results have been rationalised computationally to estimate their likely binding mode.

  报道了一系列碳水化合物-核苷酸杂交物的合成，这些杂交物被设计为多底物加合物，旨在模拟肌醇-1-磷酸合酶的首次氧化过渡态。评估了它们抑制合酶的能力，并通过计算方法对结果进行了合理化，以估计它们可能的结合模式。