(3R)-[(phenylmethoxy)methyl]-(6R)-ethyl-3,6-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester | 958737-65-0

• 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: (3R)-[(phenylmethoxy)methyl]-(6R)-ethyl-3,6-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester
• 英文别名: tert-butyl (3R,6R)-6-ethyl-1,1-dioxo-3-(phenylmethoxymethyl)-3,6-dihydrothiazine-2-carboxylate
• CAS: 958737-65-0
• 化学式: C₁₉H₂₇NO₅S
• 分子量: 381.493
• InChiKey: OMXGBOLKOWIDPZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-[(phenylmethoxy)methyl]-(6R)-ethyl-3,6-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester 在 四氧化锇 、 N-甲基吗啉氧化物 、 柠檬酸 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以78%的产率得到(3R)-[(phenylmethoxy)methyl]-(4R,5S)-dihydroxy-(6R)-ethyl-3,4,5,6-tetrahydro-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
• 作为产物：
  描述：

  tert-butyl (3S,4R)-3-((benzyloxy)methyl)-4-((dimethoxyphosphoryl)oxy)-3,4-dihydro-2H-1,2-thiazine-2-carboxylate 1,1-dioxide 、 diethylzinc 在 copper(I) cyanide*2 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以74%的产率得到(3R)-[(phenylmethoxy)methyl]-(6R)-ethyl-3,6-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

文献信息

• An RCM Strategy to Stereodiverse δ-Sultam Scaffolds
  作者：María Jiménez-Hopkins、Paul R. Hanson

  DOI：10.1021/ol800649n

  日期：2008.6.5

  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.