(R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-1-(2,3-dihydro-[1,4]-dioxino[2,3-c]pyridin-7-yl)-2-methyl-3-oxopropyl)-2-methylpropane-2-sulfinamide | 1421236-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-1-(2,3-dihydro-[1,4]-dioxino[2,3-c]pyridin-7-yl)-2-methyl-3-oxopropyl)-2-methylpropane-2-sulfinamide
• CAS: 1421236-81-8
• 化学式: C₂₇H₃₅N₃O₆S
• 分子量: 529.657
• InChiKey: JLBLVZSJPRBCSO-VZNVDEMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107.06
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  2,3-二氢[1,4]二恶并[2,3-c]吡啶-7-甲醛 在 sodium hexamethyldisilazane 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-1-(2,3-dihydro-[1,4]-dioxino[2,3-c]pyridin-7-yl)-2-methyl-3-oxopropyl)-2-methylpropane-2-sulfinamide 、 (R)-N-(3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-1-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-yl)-2-methyl-3-oxopropyl)-2-methylpropane-2-sulfinamide
  参考文献：
  名称：

  Diastereoselective Synthesis of β-Heteroaryl syn-α-Methyl-β-Amino Acid Derivatives via a Double Chiral Auxiliary Approach

  摘要：

  The addition of the SuperQuat enolate to five- and six-membered heterocyclic tert-butyl sulfinimines led to a high syn-selectivity of up to 99:1 in good to excellent yields. The reaction Is tentatively proposed to proceed through an open-chain transition state with the presence of an alpha-heteroatom on the sulfinimine leading to high diastereoselectivities. The adducts were derivatized to beta-amino esters and amides in a facile manner.

  DOI：

  10.1021/ol3033785