[2S,3S,4S,5S,5(2R,3R,4R,5R)]-3-azido-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-2-methoxy-4-methyltetrahydrofuran | 1227302-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2S,3S,4S,5S,5(2R,3R,4R,5R)]-3-azido-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-2-methoxy-4-methyltetrahydrofuran
• 英文别名: (3aR,4R,6R,6aR)-6-[(2S,3S,4S,5S)-4-azido-5-methoxy-3-methyloxolan-2-yl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 1227302-30-8
• 化学式: C₁₄H₂₃N₃O₆
• 分子量: 329.353
• InChiKey: PQUGLBPSPPUQHF-VJZZCAPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 [2S,3S,4S,5S,5(2R,3R,4R,5R)]-3-azido-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-2-methoxy-4-methyltetrahydrofuran 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以65%的产率得到[2S,3S,4S,5S,5(2R,3R,4R,5R)]-3-[N-(tert-butoxycarbonyl)amino]-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-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,4R,5S)-2-methoxy-5-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-4-methyltetrahydrofuran-3-yl trifluoromethanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以0.14 g的产率得到[2S,3S,4S,5S,5(2R,3R,4R,5R)]-3-azido-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-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