N-(iso-butyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-hydroxy-6-methylene-tetrahydro-1,2-thiazine-1,1-dioxide | 1039744-73-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-(iso-butyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-hydroxy-6-methylene-tetrahydro-1,2-thiazine-1,1-dioxide
• 英文别名: (4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-6-methylidene-2-(2-methylpropyl)-1,1-dioxothiazinan-5-ol
• CAS: 1039744-73-4
• 化学式: C₁₅H₃₁NO₄SSi
• 分子量: 349.567
• InChiKey: OOEPNUPMJRYYFB-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三乙烯二胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(iso-butyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-hydroxy-6-methylene-tetrahydro-1,2-thiazine-1,1-dioxide
  参考文献：
  名称：

  Synthesis of Sultam Scaffolds via Intramolecular Oxa-Michael and Diastereoselective Baylis−Hillman Reactions

  摘要：

  A divergent synthetic approach to new sultams utilizing intramolecular oxa-Michael and Baylis-Hillman reactions of readily prepared vinyl sulfonamides and suitably protected amino alcohols, is reported. A variety of seven- and eight-membered ring sultam scaffolds were synthesized using oxa-Michael pathways, whereas both five- and six-membered rings were synthesized using Baylis-Hillman methods. Baylis-Hillman reactions proceed with good to excellent levels of diastereoselectivity, and oxa-Michael reactions leading to eight-membered ring sultams provide empirical evidence validating 8-endo-trig cyclization pathways.

  DOI：

  10.1021/ol8009072