(2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR,5''R)-spiro[6,3',6'-trihydroxy-octahydro[2,3']bi[furo[3,2-b]furan]-3,2''-[5''-phenoxymethyl-1'',3''-oxazolidine]] | 929548-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR,5''R)-spiro[6,3',6'-trihydroxy-octahydro[2,3']bi[furo[3,2-b]furan]-3,2''-[5''-phenoxymethyl-1'',3''-oxazolidine]]
• 英文别名: (3R,3aR,6R,6aS)-6-[(2R,3'R,3'aR,5R,5'R,6'aS)-3'-hydroxy-5-(phenoxymethyl)spiro[1,3-oxazolidine-2,6'-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan]-5'-yl]-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-3,6-diol
• CAS: 929548-38-9
• 化学式: C₂₁H₂₇NO₉
• 分子量: 437.447
• InChiKey: RINMTGHPAFTUHA-GFAINMBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR,5''R)-spiro[6,3',6'-trihydroxy-octahydro[2,3']bi[furo[3,2-b]furan]-3,2''-[5''-phenoxymethyl-1'',3''-oxazolidine]] 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2R)-1-氨基-3-苯氧基-2-丙醇
  参考文献：
  名称：

  Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary

  摘要：

  An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active P-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.01.039
• 作为产物：
  描述：

  1,4:3,6-dianhydro-D-fructose 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (2R,3R,3aS,6R,6aR,3'R,3'aS,6'R,6'aR,5''R)-spiro[6,3',6'-trihydroxy-octahydro[2,3']bi[furo[3,2-b]furan]-3,2''-[5''-phenoxymethyl-1'',3''-oxazolidine]]
  参考文献：
  名称：

  A novel free C-12 higher carbon sugar: asymmetric synthesis and reactivity with nucleophiles

  摘要：

  A novel C-12 higher carbon sugar, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)- 1,4:3,6-dianhydro-D-fructose, was firstly synthesized via a convenient aldol reaction of 1,4:3,6-dianhydro-D-fructose without any protection and activation of functional groups. The reactivity of the novel higher sugar with nucleophiles was also studied, through which a series of oxazolidines and other derivatives of the higher sugar were available. The study showed that the higher sugar possesses a highly reactive carbonyl group and a good stereo controlling ability in the reaction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.042

文献信息

• Non-enzymatic kinetic resolution of β-amino alcohols using C-12 higher carbon sugar as a chiral auxiliary
  作者：Jing-Yu Zhang、Hong-Min Liu、Hai-Wei Xu、Li-Hong Shan

  DOI：10.1016/j.tetasy.2008.01.039

  日期：2008.3

  An efficient non-enzymatic kinetic resolution strategy capable of accessing optically active P-adrenergic antagonists intermediates is reported. The C-12 higher carbon sugar derived from naturally occurring sucrose was employed to probe the kinetic resolution. Excellent enantiomeric excesses (ee >99%) and high yields were obtained under very mild conditions. The chiral auxiliary could be recovered in a high reclaimed ratio (>95%) and reusable form without any decrease of the resolving ability. (C) 2008 Published by Elsevier Ltd.
• A novel free C-12 higher carbon sugar: asymmetric synthesis and reactivity with nucleophiles
  作者：Hong-Min Liu、Feng-Wu Liu、Xiao-Ping Song、Jing-Yu Zhang、Lin Yan

  DOI：10.1016/j.tetasy.2006.11.042

  日期：2006.12

  A novel C-12 higher carbon sugar, (1R)-(1,4:3,6-dianhydro-D-mannitol-2-yl)- 1,4:3,6-dianhydro-D-fructose, was firstly synthesized via a convenient aldol reaction of 1,4:3,6-dianhydro-D-fructose without any protection and activation of functional groups. The reactivity of the novel higher sugar with nucleophiles was also studied, through which a series of oxazolidines and other derivatives of the higher sugar were available. The study showed that the higher sugar possesses a highly reactive carbonyl group and a good stereo controlling ability in the reaction. (c) 2006 Elsevier Ltd. All rights reserved.