(S)-N-(2-(tert-butyldimethylsilyloxy)-3-(trityloxy)propyl)-N-isobutylethenesulfonamide | 1039744-71-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (S)-N-(2-(tert-butyldimethylsilyloxy)-3-(trityloxy)propyl)-N-isobutylethenesulfonamide
• 英文别名: N-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-3-trityloxypropyl]-N-(2-methylpropyl)ethenesulfonamide
• CAS: 1039744-71-2
• 化学式: C₃₄H₄₇NO₄SSi
• 分子量: 593.903
• InChiKey: FYYWMWVXEXUKLZ-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-(2-(tert-butyldimethylsilyloxy)-3-(trityloxy)propyl)-N-isobutylethenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以92%的产率得到2-isobutyl-(4S)-(trityloxymethyl)-5,1,2-oxathiazepine-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
• 作为产物：
  描述：

  2-氯乙烷磺酰氯 、 (S)-2-(tert-butyldimethylsilyloxy)-N-isobutyl-3-(trityloxy)propan-1-amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(S)-N-(2-(tert-butyldimethylsilyloxy)-3-(trityloxy)propyl)-N-isobutylethenesulfonamide
  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

文献信息

• Synthesis of Sultam Scaffolds via Intramolecular Oxa-Michael and Diastereoselective Baylis−Hillman Reactions
  作者：Aihua Zhou、Paul R. Hanson

  DOI：10.1021/ol8009072

  日期：2008.7.17

  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.