(R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-2,3-dihydro-furan | 223664-56-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-2,3-dihydro-furan
• CAS: 223664-56-0
• 化学式: C₂₈H₄₂O₃Si₂
• 分子量: 482.811
• InChiKey: UHZFERKZVRDGKW-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (3R,5R,6R)-2-acetoxy-5-(2,2-dimethyl-propionyloxy)-6-methyl-tetrahydro-pyran-3-yl ester 、 (R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-2,3-dihydro-furan 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 、
  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 咪唑 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-2,3-dihydro-furan
  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