(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one | 96199-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
• 英文别名: (4S)-4r,5c-(S,R)-bis-(2,2-dimethyl-[1,3]dioxolan-4-yl)-oxazolidin-2-one；N,O⁴-carbonyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-altritol-3-ylamine；3-N-4-O-Carbonyl-3-amino-3-desoxy-1,2;5,6-di-O-isopropyliden-D-altrit；(4S,5S)-4,5-bis[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
• CAS: 96199-45-0
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: LCTHPXTYPXUBFC-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one 在 正丁基锂 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (4S,5S,2'R,3'R)-3-(3-hydroxy-2-methyl-3-phenyl-1-oxopropyl)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  DIASTEREOSELECTIVE ALKYLATION AND ALDOL REACTIONS MEDIATED BY THE d-MANNITOL-DERIVED OXAZOLIDIN-2-ONE AS A CHIRAL AUXILIARY

  摘要：

  Chiral N-acylated oxazolidin-2-ones readily available from D-mannitol have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide Z-enolates to afford a-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base.

  DOI：

  10.1081/scc-120015404
• 作为产物：
  描述：

  1,2:5,6-di-O-isopropyliden-3-(phenoxycarbonylamino)-3-desoxy-D-altrit 以 吡啶 为溶剂， 生成 (4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthetic Nucleosides. LXII.^1,2 Facile Displacement Reactions in the D-Mannitol Series. V. Studies on the Selective Conversion of Some Hexitol Derivatives to Aldoses

  摘要：

  DOI：

  10.1021/jo01028a019

文献信息

• Stereoselective Synthesis of β‐Lactams by Using D‐Mannitol‐Derived Oxazolidin‐2‐one as a Chiral Auxiliary
  作者：Dong Gyun Shin、Hye Jin Heo、Jong‐Gab Jun

  DOI：10.1081/scc-200050961

  日期：2005.3

  have been demonstrated to undergo highly diastereoselective β‐lactam synthesis via the Staudinger reaction with Mukaiyama reagent. Stereoselectivity for cis‐β‐lactam was the result of the [2 + 2] cycloaddition reaction of ketene to trans imines, and cyclohexylidene showed better yield and stereoselectivity than the isopropylidene auxiliary.

  摘要 含有异亚丙基和亚环己基官能团的手性恶唑烷-2-酮，容易从 D-甘露醇中获得，已被证明通过与 Mukaiyama 试剂的 Staudinger 反应进行高度非对映选择性的 β-内酰胺合成。顺式-β-内酰胺的立体选择性是烯酮与反式亚胺的[2+2]环加成反应的结果，环己叉的收率和立体选择性优于异丙叉辅助剂。