[2S,3S,4S,5S,5(2R,3S)]-3-azido-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran | 1227302-31-9

• 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: [2S,3S,4S,5S,5(2R,3S)]-3-azido-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran
• 英文别名: (4S,5S)-4-[(2S,3S,4S,5S)-4-azido-5-methoxy-3-methyloxolan-2-yl]-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolane
• CAS: 1227302-31-9
• 化学式: C₁₉H₂₇N₃O₅
• 分子量: 377.44
• InChiKey: BFQRCGBBIYVTHY-BULOIVJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S,3R,4R,5S)-5-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-methoxy-4-methyltetrahydrofuran-3-yl trifluoromethanesulfonate 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 以26 mg的产率得到[2S,3S,4S,5S,5(2R,3S)]-3-azido-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-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