(3R,5R)-5-(hydroxymethyl)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]oxolan-2-ol | 223663-69-2

• 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: (3R,5R)-5-(hydroxymethyl)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]oxolan-2-ol
• CAS: 223663-69-2
• 化学式: C₂₇H₃₆O₆
• 分子量: 456.579
• InChiKey: DIUUNBIRSYQOPO-YZBRRSJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,5R)-5-(hydroxymethyl)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]oxolan-2-ol 以70%的产率得到(S)-4-((2S,3R,5R,6R)-3,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-4-methyl-5-methylene-pyrrolidin-2-one
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate

  摘要：

  Four monocyclic precursors were assembled in the total synthesis of the proposed structure 1-A of (+)-tolyporphin A O,O-diacetate (X=Ac). Comparison of the spectroscopic data demonstrated that synthetic tolyporphin O,O-diacetate did not match the O,O-diacetate prepared from natural (+)-tolyporphin A (X=H), calling for a structural revision of this class of natural products. On the basis of a series of NMR experiments including synthetic intermediates, the structure of tolyporphin A is concluded to be 1-B, in which the configurations of quaternary centers C7 and C17 are opposite to those in the originally proposed structure.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<923::aid-anie923>3.0.co;2-7
• 作为产物：
  描述：

  (R)-γ-羟甲基-γ-丁内酯 (R)-4,5-二氢-5-羟甲基-2(3H)-呋喃酮 (R)-5-羟甲基-2-氧代四氢呋喃 在 三氟甲磺酸三甲基硅酯 、 硫酸 、 magnesium sulfate 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R,5R)-5-(hydroxymethyl)-2,3-dimethyl-3-[(2S,3R,5R,6R)-6-methyl-3,5-bis(phenylmethoxy)oxan-2-yl]oxolan-2-ol
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate

  摘要：

  Four monocyclic precursors were assembled in the total synthesis of the proposed structure 1-A of (+)-tolyporphin A O,O-diacetate (X=Ac). Comparison of the spectroscopic data demonstrated that synthetic tolyporphin O,O-diacetate did not match the O,O-diacetate prepared from natural (+)-tolyporphin A (X=H), calling for a structural revision of this class of natural products. On the basis of a series of NMR experiments including synthetic intermediates, the structure of tolyporphin A is concluded to be 1-B, in which the configurations of quaternary centers C7 and C17 are opposite to those in the originally proposed structure.

  DOI：

  10.1002/(sici)1521-3773(19990401)38:7<923::aid-anie923>3.0.co;2-7