(3S,4S)-3-[(phenylmethoxy)methyl]-4-hydroxy-3,4-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester | 1028072-14-1

• 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: (3S,4S)-3-[(phenylmethoxy)methyl]-4-hydroxy-3,4-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester
• 英文别名: tert-butyl (3S,4R)-4-hydroxy-1,1-dioxo-3-(phenylmethoxymethyl)-3,4-dihydrothiazine-2-carboxylate
• CAS: 1028072-14-1
• 化学式: C₁₇H₂₃NO₆S
• 分子量: 369.439
• InChiKey: GZXZWDHQXBZQPQ-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到tert-butyl [(3S,4R)-1,1-dioxo-3-(phenylmethoxymethyl)-3,4-dihydro-2H-thiazin-4-yl] carbonate
  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：

  tert-butyl (3aS,7S,7aS)-7-((benzyloxy)methyl)-2-oxotetrahydro-6H-[1,3]dioxolo[4,5-d][1,2]thiazine-6-carboxylate 5,5-dioxide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(3S,4S)-3-[(phenylmethoxy)methyl]-4-hydroxy-3,4-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester
  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