[2S,3R,4S,5S,5(2R,3S)]-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran-3-ol | 1227302-21-7

• 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,3R,4S,5S,5(2R,3S)]-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran-3-ol
• 英文别名: (2S,3R,4S,5S)-5-[(4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-1,3-dioxolan-4-yl]-2-methoxy-4-methyloxolan-3-ol
• CAS: 1227302-21-7
• 化学式: C₁₉H₂₈O₆
• 分子量: 352.428
• InChiKey: VFCQGVAXGFWCGU-KJGIYEQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 [2S,3R,4S,5S,5(2R,3S)]-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran-3-ol 在 吡啶 作用下， 生成 (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
  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：

  甲醇 、 (3R,4S,5R,6S)-7-O-benzyl-1,2-epoxy-4,5,6,7-tetrahydroxy-5,6-O-isopropylidene-3-methylheptyl N,N-diisopropylcarbamate 在 acide methanesulfonique 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以69%的产率得到[2S,3R,4S,5S,5(2R,3S)]-5-(3-O-benzyl-1,2,3-trihydroxy-1,2-O-isopropylidene)-2-methoxy-4-methyltetrahydrofuran-3-ol
  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