benzyl (5S)-5-[(S)-[(2R,4R)-2-tert-butyl-2-methyl-5-oxo-1,3-dioxan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 1155868-37-3

• 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: benzyl (5S)-5-[(S)-[(2R,4R)-2-tert-butyl-2-methyl-5-oxo-1,3-dioxan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1155868-37-3
• 化学式: C₂₃H₃₃NO₇
• 分子量: 435.518
• InChiKey: RCEOYQRPOZGUIZ-KEXUJGGDSA-N

物化性质

• 沸点：
  559.7±50.0 °C(predicted)
• 密度：
  1.188±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-benzyl 5-(dihydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate 、 2-tert-butyl-2-methyl-1,3-dioxan-5-one 在 D-脯氨酸 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 以58%的产率得到benzyl (5S)-5-[(S)-[(2R,4R)-2-tert-butyl-2-methyl-5-oxo-1,3-dioxan-4-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Organocatalytic syn-Aldol Reactions of Dioxanones with (S)-Isoserinal Hydrate: Synthesis of l-Deoxymannojirimycin and l-Deoxyidonojirimycin

  摘要：

  We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.

  DOI：

  10.1021/jo900263s

文献信息

• Synthesis of higher carbon sugars from dihydroxyacetone and d-arabinose: an organocatalytic approach
  作者：Maciej Cieplak、Magdalena Ceborska、Piotr Cmoch、Sławomir Jarosz

  DOI：10.1016/j.tetasy.2012.07.012

  日期：2012.8

  The reaction of 2,3:4,5-diacetone-D-arabinose with protected dihydroxyacetone catalyzed by L-proline afforded two diastereoisomeric octoses in a 7:1 ratio in 75% yield. The anti (3S,4S) configuration at the newly created stereogenic centers was assigned to the main isomer on the basis of the X-ray analysis. The same reaction when catalyzed with unnatural D-proline provided the same products in a 1:20 ratio. (c) 2012 Elsevier Ltd. All rights reserved.
• Organocatalytic <i>syn</i>-Aldol Reactions of Dioxanones with (<i>S</i>)-Isoserinal Hydrate: Synthesis of <scp>l</scp>-Deoxymannojirimycin and <scp>l</scp>-Deoxyidonojirimycin
  作者：Nagarjuna Palyam、Marek Majewski

  DOI：10.1021/jo900263s

  日期：2009.6.5

  We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.