[(2S,3R,4R,5S)-2-methoxy-4-methyl-5-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]oxolan-3-yl] trifluoromethanesulfonate | 1227302-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4R,5S)-2-methoxy-4-methyl-5-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]oxolan-3-yl] trifluoromethanesulfonate
• CAS: 1227302-23-9
• 化学式: C₁₈H₂₇F₃O₁₀S
• 分子量: 492.468
• InChiKey: JDYZPAMZUXKJAU-BBEZQUJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4R,5S)-2-methoxy-4-methyl-5-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]oxolan-3-yl] trifluoromethanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以0.12 g的产率得到[2S,3S,4S,5S,5(2R,3S,4S,5R,6R)]-3-azido-5-(3,4,5,6-tetrahydroxy-3,4;5,6-di-O-isopropylidene-2-tetrahydropyranyl)-2-methoxy-4-methyltetrahydrofuran
  参考文献：
  名称：

  Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes

  摘要：

  A flexible strategy for the stereoselective synthesis of branched amino sugar analogues is described. It is based on a C-3-chain elongation of suitable protected aldoses. By using the sequence homoaldol reaction, epoxidation, and methanolysis alpha-methyl allo-furanosides are obtained. Proximate amination of the corresponding triflates afford the title compounds. All reactions proceed with high yield, high diastereoselectivities, and allow for a broad application.

  DOI：

  10.1055/s-0029-1218628
• 作为产物：
  描述：

  [2S,3R,4S,5S,5(2R,3S,4S,5R,6R)]-5-(3,4,5,6-tetrahydroxy-3,4:5,6-di-O-isopropylidene-2-tetrahydropyranyl)-2-methoxy-4-methyltetrahydrofuran-3-ol 、 三氟甲磺酸酐 在 吡啶 作用下， 生成 [(2S,3R,4R,5S)-2-methoxy-4-methyl-5-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]oxolan-3-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes

  摘要：

  A flexible strategy for the stereoselective synthesis of branched amino sugar analogues is described. It is based on a C-3-chain elongation of suitable protected aldoses. By using the sequence homoaldol reaction, epoxidation, and methanolysis alpha-methyl allo-furanosides are obtained. Proximate amination of the corresponding triflates afford the title compounds. All reactions proceed with high yield, high diastereoselectivities, and allow for a broad application.

  DOI：

  10.1055/s-0029-1218628