[2S,3S,4S,5S,5(1R)]-3-azido-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran | 1227302-27-3

• 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(1R)]-3-azido-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran
• 英文别名: (4R)-4-[(2S,3S,4S,5S)-4-azido-5-methoxy-3-methyloxolan-2-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 1227302-27-3
• 化学式: C₁₁H₁₉N₃O₄
• 分子量: 257.29
• InChiKey: YNECVXQPETXIPR-SVSWQMSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 [2S,3S,4S,5S,5(1R)]-3-azido-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran 在 1% Pd/C 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 [2S,3S,4S,5S,5(1R)]-3-[N-(tert-butoxycarbonyl)amino]-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran
  参考文献：
  名称：

  Highly stereoselective De-Novo synthesis of protected 2-amino-3-C-methyl-2,3-dideoxy-d-altrose

  摘要：

  A new strategy for the stereoselective synthesis of 2-amino-2-deoxy-aldoses is described. Therefore epoxy carbamates are reacted with isocyanates to furnish urethanes, which will form the title compounds with high diastereoselectivities under basic conditions and O,O-migration of the carbamoyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.101
• 作为产物：
  描述：

  [2S,3R,4S,5S,5(1R)]-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran-3-ol 在 吡啶 、 三氟甲磺酸酐 、 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 [2S,3S,4S,5S,5(1R)]-3-azido-5-(1,2-dihydroxy-1,2-O-isopropylideneethyl)-2-methoxy-4-methyltetrahydrofuran
  参考文献：
  名称：

  Highly stereoselective De-Novo synthesis of protected 2-amino-3-C-methyl-2,3-dideoxy-d-altrose

  摘要：

  A new strategy for the stereoselective synthesis of 2-amino-2-deoxy-aldoses is described. Therefore epoxy carbamates are reacted with isocyanates to furnish urethanes, which will form the title compounds with high diastereoselectivities under basic conditions and O,O-migration of the carbamoyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.101

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.