tert-butyl (3S,4R)-3-((benzyloxy)methyl)-4-((dimethoxyphosphoryl)oxy)-3,4-dihydro-2H-1,2-thiazine-2-carboxylate 1,1-dioxide | 1028072-55-0

• 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: tert-butyl (3S,4R)-3-((benzyloxy)methyl)-4-((dimethoxyphosphoryl)oxy)-3,4-dihydro-2H-1,2-thiazine-2-carboxylate 1,1-dioxide
• CAS: 1028072-55-0
• 化学式: C₁₉H₂₈NO₉PS
• 分子量: 477.472
• InChiKey: ACOQGKSCKIFXPK-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  117.67
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,4R)-3-((benzyloxy)methyl)-4-((dimethoxyphosphoryl)oxy)-3,4-dihydro-2H-1,2-thiazine-2-carboxylate 1,1-dioxide 在 iron(III) chloride 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以60%的产率得到(3S,4R)-3-((benzyloxy)methyl)-1,1-dioxido-3,4-dihydro-2H-1,2-thiazin-4-yl dimethyl phosphate
  参考文献：
  名称：

  An RCM Strategy to Stereodiverse δ-Sultam Scaffolds

  摘要：

  An asymmetric approach for the synthesis of substituted delta-sultams with multiple synthetic handles is described. This study demonstrates the facile construction of a stereochemically diverse array of substituted delta-sultams, more specifically substituted 3,4,5,6-dihydro 1,2-thiazine 1,1-dioxides. A pivotal Mitsunobu alkylation/RCM sequence is used to assemble key allyl sultam building blocks possessing a C3 stereogenic handle. All subsequent reactions are achieved with high levels of diastereoselectivity to afford enantiopure delta-sultams in good yields.

  DOI：

  10.1021/ol800649n
• 作为产物：
  描述：

  (3S,4S)-3-[(phenylmethoxy)methyl]-4-hydroxy-3,4-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester 、 氯磷酸二甲酯 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到tert-butyl (3S,4R)-3-((benzyloxy)methyl)-4-((dimethoxyphosphoryl)oxy)-3,4-dihydro-2H-1,2-thiazine-2-carboxylate 1,1-dioxide
  参考文献：
  名称：

  An RCM Strategy to Stereodiverse δ-Sultam Scaffolds

  摘要：

  An asymmetric approach for the synthesis of substituted delta-sultams with multiple synthetic handles is described. This study demonstrates the facile construction of a stereochemically diverse array of substituted delta-sultams, more specifically substituted 3,4,5,6-dihydro 1,2-thiazine 1,1-dioxides. A pivotal Mitsunobu alkylation/RCM sequence is used to assemble key allyl sultam building blocks possessing a C3 stereogenic handle. All subsequent reactions are achieved with high levels of diastereoselectivity to afford enantiopure delta-sultams in good yields.

  DOI：

  10.1021/ol800649n