[3R,4S,4(2R,3R,4R,5R)]-1,2-epoxy-4-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-4-hydroxy-3-methylbutyl N,N-diisopropylcarbamate | 1227302-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3R,4S,4(2R,3R,4R,5R)]-1,2-epoxy-4-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-4-hydroxy-3-methylbutyl N,N-diisopropylcarbamate
• CAS: 1227302-17-1
• 化学式: C₂₀H₃₅NO₈
• 分子量: 417.5
• InChiKey: NDFGCLPGIAIDIF-UMCVGDSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  99.22
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 [3R,4S,4(2R,3R,4R,5R)]-1,2-epoxy-4-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-4-hydroxy-3-methylbutyl N,N-diisopropylcarbamate 在 acide methanesulfonique 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以73%的产率得到[2S,3R,4S,5S,5(2R,3R,4R,5R)]-5-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-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
• 作为产物：
  描述：

  [Z,3S,4S,4(2R,3R,4R,5R)]-4-hydroxy-4-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-3-methylbut-1-enyl N,N-diisopropylcarbamate 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以85%的产率得到[3R,4S,4(2R,3R,4R,5R)]-1,2-epoxy-4-(3,4,5-trihydroxy-3,4-O-isopropylidene-5-O-methyl-2-tetrahydrofuranyl)-4-hydroxy-3-methylbutyl N,N-diisopropylcarbamate
  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