(S)-benzyl 5-(dihydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate | 1155868-20-4

• 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: (S)-benzyl 5-(dihydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate
• 英文别名: benzyl (5S)-5-(dihydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1155868-20-4
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: WXYXAELZMICBAR-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 5-(dihydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate 、 2-tert-butyl-2-methyl-1,3-dioxan-5-one 在 L-脯氨酸 、 lithium bromide 作用下， 以 二甲基亚砜 为溶剂， 反应 96.0h， 以69%的产率得到benzyl (5S)-5-[(R)-[(2R,4S)-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：

  Synthesis of higher carbon sugars from dihydroxyacetone and d-arabinose: an organocatalytic approach

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2012.07.012
• 作为产物：
  描述：

  (5S)-5-甲酰基-2,2-二甲基-1,3-恶唑烷-3-羧酸苄酯 在 水 作用下， 生成 (S)-benzyl 5-(dihydroxymethyl)-2,2-dimethyloxazolidine-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

• Organocatalytic<i>syn</i>-Aldol Reactions of Hydroxy Ketones with (<i>S</i>)-Isoserinal: Asymmetric Synthesis of 6-Deoxy-1,5-iminohexitols and Related Compounds
  作者：Cyril Nicolas、Roman Pluta、Monika Pasternak-Suder、Olivier R. Martin、Jacek Mlynarski

  DOI：10.1002/ejoc.201201413

  日期：2013.3

  intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a (L-manno) and 10b (D-gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)-isoserinal hydrate and hydroxyacetone or

  报道了一种改进且方便的大规模保护 (S)-异丝氨酸制备方法。该关键中间体通过有机催化的羟醛反应或基于 Wittig 的扩链和官能化反应，得到对映体纯的 1,5,6-trideoxy-1,5-imino-hexitols，如 10a (L-manno) 和 10b (D-gluco)。这两种化合物可用作糖苷酶抑制剂。精心设计的有机催化过程包括 (S)-异丝氨酸水合物与羟基丙酮或 1-羟基-2-辛酮的非对映选择性合成羟醛反应，并由各种基于氨基酸的催化剂促进。实现了高达 8:1 的非对映选择性，从而为这些重要的碳水化合物模拟物建立了一条新的、有效的合成路线。