1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofurano[2,3-d][1,3]dioxol-5-yl]ethanol | 221372-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofurano[2,3-d][1,3]dioxol-5-yl]ethanol
• 英文别名: 1-((3aR,5S,6aR)-2,2-Dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol；((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol；1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol
• CAS: 221372-79-8
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: QNHJMWCBQTWWSC-UNYLCCJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofurano[2,3-d][1,3]dioxol-5-yl]ethanol 在 palladium dihydroxide 、 palladium on activated charcoal 咪唑 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 2SPh2 、 D(+)-10-樟脑磺酸 、 水 、 氢气 、 碘 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 zinc(II) chloride 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 、 paraffin 、 苯 为溶剂， 反应 60.75h， 生成 (2R,3S,4aR,8S,9aS)-3-Hydroxy-2,8-dimethyl-2-propyl-octahydro-1,5-dioxa-benzocyclohepten-6-one
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

  摘要：

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 高碘酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 1-[(3aS,5S,6aS)-2,2-dimethyl-3a,5,6,6a-tetrahydrofurano[2,3-d][1,3]dioxol-5-yl]ethanol
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

  摘要：

  Discussed herein is our first generation strategy for the total synthesis of brevetoxin A. This approach relies upon dissection of the molecule at the nine-membered ring site (ring E), A Wittig coupling of requisite polycyclic fragments 3 and 4 followed by hydroxy dithioketal cyclization was expected to furnish the polycyclic framework of brevetoxin A (1). Intermediate 8 was anticipated to be a valid synthetic precursor to phosphonium salt 3, and its synthesis was accomplished by a bis(lactonization)/thionolactone formation/functionalization sequence. In order to test our synthetic strategy, the synthesis of an advanced model system (36) was attempted. Aldehyde 38 and phosphonium salt 37 were successfully synthesized and coupled through a:Wittig reaction. Unfortunately, the planned hydroxy dithioketal cyclization to form the crucial nonacene (ring E) did not proceed as anticipated and this synthetic approach was discontinued.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<599::aid-chem599>3.0.co;2-n

文献信息

• NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2,7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160194350A1

  公开（公告）日：2016-07-07

  The present invention relates to compounds of formula (I), wherein R 1 , R 2 and R 3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  本发明涉及式(I)的化合物，其中R1、R2和R3如本文所述，以及它们的前药或药用可接受的盐、对映体或二对映体，以及包括这些化合物的组合物和使用这些化合物的方法。
• TLR7 AGONISTS
  申请人：Primmune Therapeutics, Inc.

  公开号：US20210155652A1

  公开（公告）日：2021-05-27

  The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.

  本发明涉及根据式I的TLR7激动剂及其在治疗癌症和传染病等疾病中的应用。
• 3-substituted 5-amino-6H-thiazolo[4,5-d]pyrimidine-2,7-dione compounds for the treatment and prophylaxis of virus infection
  申请人：Hoffmann-La Roche Inc.

  公开号：US10040815B2

  公开（公告）日：2018-08-07

  The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

  本发明涉及式（I）化合物、 其中 R1、R2 和 R3 如本文所述，及其原药或药学上可接受的盐、对映体或非对映异构体，以及包括这些化合物的组合物和使用这些化合物的方法。
• NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2, 7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION
  申请人：Hoffmann-La Roche Inc.

  公开号：US20160326209A1

  公开（公告）日：2016-11-10

  The present invention relates to compounds of formula (I), wherein R 1 , R 2 and R 3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.
• US9441008B2
  申请人：——

  公开号：US9441008B2

  公开（公告）日：2016-09-13