[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

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: [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
• 英文别名: (2S,3R,4S,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-ol
• 化学式: C₁₇H₂₈O₈
• 分子量: 360.405
• InChiKey: BHOZRBGNVPBJHO-ZKGSJSDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  [Z,3S,4S,4(2R,3S,4S,5R,6R)]-4-(3,4,5,6-tetrahydroxy-3,4:5,6-di-O-isopropylidene-2-tetrahydropyranyl)-4-hydroxy-3-methylbut-1-enyl N,N-diisopropylcarbamate 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 甲烷磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 [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
  参考文献：
  名称：

  糖醛的链延长不对称 Homoaldol 反应：引入功能化的 3-甲基取代的三碳单元

  摘要：

  O-保护的醛糖与 α-钛化巴豆基 N，N-二异丙基氨基甲酸酯反应生成链延长的 1-烯基氨基甲酸酯。这些通过双键的环氧化和随后的甲醇分解进一步官能化以形成甲基3-C-甲基-3-脱氧-呋喃糖苷。Mukaiyama 型添加苯甲醛导致四取代的四氢呋喃。所有反应都以高非对映选择性进行，并允许广泛应用。

  DOI：

  10.1055/s-2007-965928

文献信息

• Highly Stereoselective Synthesis of 2-Amino-3-C-methyl-2,3-dideoxyaldoses by C3-Chain Elongation via Homoaldol Reaction of Sugar Aldehydes
  作者：Dieter Hoppe、Sabine Kollmann、Roland Fröhlich

  DOI：10.1055/s-0029-1218628

  日期：2010.3

  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.
• Chain-Elongation of Sugar Aldehydes by Asymmetric Homoaldol Reaction: Introduction of a Functionalized 3-Methyl-Substituted Three-Carbon Unit
  作者：Dieter Hoppe、Sabine Kollmann、Roland Fröhlich

  DOI：10.1055/s-2007-965928

  日期：2007.3

  by epoxidation of the double bond and subsequent methanolysis to form methyl 3- C-methyl-3-deoxy-furanosides. Mukaiyama-type addition of benzaldehyde led to tetrasubstituted tetrahydrofurans. All reactions proceeded with high diastereoselectivities and allow for a broad application.

  O-保护的醛糖与 α-钛化巴豆基 N，N-二异丙基氨基甲酸酯反应生成链延长的 1-烯基氨基甲酸酯。这些通过双键的环氧化和随后的甲醇分解进一步官能化以形成甲基3-C-甲基-3-脱氧-呋喃糖苷。Mukaiyama 型添加苯甲醛导致四取代的四氢呋喃。所有反应都以高非对映选择性进行，并允许广泛应用。