2-Deoxy-4,5-O-isopropylidene-3-O-methyl-7-O-tosyl-D-manno-heptose trimethylene dithioacetal | 162879-67-6

• 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-Deoxy-4,5-O-isopropylidene-3-O-methyl-7-O-tosyl-D-manno-heptose trimethylene dithioacetal
• 英文别名: [(2R)-2-[(4R,5R)-5-[(1R)-2-(1,3-dithian-2-yl)-1-methoxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl] 4-methylbenzenesulfonate
• CAS: 162879-67-6
• 化学式: C₂₁H₃₂O₇S₃
• 分子量: 492.679
• InChiKey: CHCPAEATCZDKOR-HNBVOPMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-Deoxy-4,5-O-isopropylidene-3-O-methyl-7-O-tosyl-D-manno-heptose trimethylene dithioacetal 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到6,7-Anhydro-2-deoxy-4,5-O-isopropylidene-3-O-methyl-D-manno-heptose trimethylene dithioacetal
  参考文献：
  名称：

  From Sugars to Carbocycles. 2. Three- to Seven-Membered Rings from Mannose by Addition of 1,3-Dithiane Followed by Intramolecular Displacement Reaction

  摘要：

  A new methodology for the conversion of sugars to three-, four-, six-, and seven-membered rings is presented. The sequence of transformations is demonstrated with mannose (1) and involves addition of 2-lithio-1,3-dithiane to the acetonide 2 followed by elimination and reduction to the 2-deoxy-dithiane 6. Starting from this intermediate, appropriate activation (tosylate, epoxide) and protection (acetonide, methyl ether) yields 8, 18, and 23, the starting materials for carbocyclization, which are converted by nucleophile displacement to the optically active cyclopropane 9, cyclobutane 19, cyclohexane 24, and cycloheptane 25, respectively. The cyclopropyl-1,3-dithane 9 can be desulfurized to the cyclopropane 10.

  DOI：

  10.1021/jo00099a043
• 作为产物：
  描述：

  2-Deoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptose trimethylene dithioacetal 在 吡啶 、 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 44.0h， 生成 2-Deoxy-4,5-O-isopropylidene-3-O-methyl-7-O-tosyl-D-manno-heptose trimethylene dithioacetal
  参考文献：
  名称：

  From Sugars to Carbocycles. 2. Three- to Seven-Membered Rings from Mannose by Addition of 1,3-Dithiane Followed by Intramolecular Displacement Reaction

  摘要：

  A new methodology for the conversion of sugars to three-, four-, six-, and seven-membered rings is presented. The sequence of transformations is demonstrated with mannose (1) and involves addition of 2-lithio-1,3-dithiane to the acetonide 2 followed by elimination and reduction to the 2-deoxy-dithiane 6. Starting from this intermediate, appropriate activation (tosylate, epoxide) and protection (acetonide, methyl ether) yields 8, 18, and 23, the starting materials for carbocyclization, which are converted by nucleophile displacement to the optically active cyclopropane 9, cyclobutane 19, cyclohexane 24, and cycloheptane 25, respectively. The cyclopropyl-1,3-dithane 9 can be desulfurized to the cyclopropane 10.

  DOI：

  10.1021/jo00099a043

文献信息

• From Sugars to Carbocycles. 2. Three- to Seven-Membered Rings from Mannose by Addition of 1,3-Dithiane Followed by Intramolecular Displacement Reaction
  作者：Karsten Krohn、Guido Boerner

  DOI：10.1021/jo00099a043

  日期：1994.10

  A new methodology for the conversion of sugars to three-, four-, six-, and seven-membered rings is presented. The sequence of transformations is demonstrated with mannose (1) and involves addition of 2-lithio-1,3-dithiane to the acetonide 2 followed by elimination and reduction to the 2-deoxy-dithiane 6. Starting from this intermediate, appropriate activation (tosylate, epoxide) and protection (acetonide, methyl ether) yields 8, 18, and 23, the starting materials for carbocyclization, which are converted by nucleophile displacement to the optically active cyclopropane 9, cyclobutane 19, cyclohexane 24, and cycloheptane 25, respectively. The cyclopropyl-1,3-dithane 9 can be desulfurized to the cyclopropane 10.