(3S,4R,5S)-3-[(phenylmethoxy)methyl]-4,5-dihydroxy-3,4,5,6-tetrahydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester | 958737-50-3

• 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,4R,5S)-3-[(phenylmethoxy)methyl]-4,5-dihydroxy-3,4,5,6-tetrahydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester
• 英文别名: tert-butyl (3S,4S,5S)-4,5-dihydroxy-1,1-dioxo-3-(phenylmethoxymethyl)thiazinane-2-carboxylate
• CAS: 958737-50-3
• 化学式: C₁₇H₂₅NO₇S
• 分子量: 387.454
• InChiKey: WMZNKJWZAWLABN-ZNMIVQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三光气 、 (3S,4R,5S)-3-[(phenylmethoxy)methyl]-4,5-dihydroxy-3,4,5,6-tetrahydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethylethyl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到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
  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：

  (3R)-3-[(phenylmethoxy)methyl]-3,6-dihydro-1,2-thiazine-N-carboxylic acid 1,1-dioxide 1,1-dimethyl-ethyl 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96%的产率得到(3S,4R,5S)-3-[(phenylmethoxy)methyl]-4,5-dihydroxy-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

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.