tert-butyl (3aS,7S,7aR)-2,5,5-trioxo-7-(phenylmethoxymethyl)-3-propan-2-yl-3a,4,7,7a-tetrahydro-[1,3]oxazolo[5,4-d]thiazine-6-carboxylate | 1028072-44-7

• 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 (3aS,7S,7aR)-2,5,5-trioxo-7-(phenylmethoxymethyl)-3-propan-2-yl-3a,4,7,7a-tetrahydro-[1,3]oxazolo[5,4-d]thiazine-6-carboxylate
• CAS: 1028072-44-7
• 化学式: C₂₁H₃₀N₂O₇S
• 分子量: 454.544
• InChiKey: WUWKZIQPYYVWCT-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 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 、 异氰酸异丙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到tert-butyl (3aS,7S,7aR)-2,5,5-trioxo-7-(phenylmethoxymethyl)-3-propan-2-yl-3a,4,7,7a-tetrahydro-[1,3]oxazolo[5,4-d]thiazine-6-carboxylate
  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.