(S)-4-isopropyl-3,4-dimethyl-1,2,3-oxathiazolidine 2,2-dioxide | 1370547-43-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: (S)-4-isopropyl-3,4-dimethyl-1,2,3-oxathiazolidine 2,2-dioxide
• 英文别名: (4S)-3,4-dimethyl-4-propan-2-yloxathiazolidine 2,2-dioxide
• CAS: 1370547-43-5
• 化学式: C₇H₁₅NO₃S
• 分子量: 193.267
• InChiKey: AKVXIMVFLOGGMF-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-isopropyl-3,4-dimethyl-1,2,3-oxathiazolidine 2,2-dioxide 在 3,5-二甲基吡唑 、 chromium(VI) oxide 、 甲酸 、 亚硝酸特丁酯 、 palladium 10% on activated carbon 、 20 wt.% Pd(OH)2 on activated carbon 、 氨 、 氢气 、 potassium 2-methylbutan-2-olate 、 sodium cyanoborohydride 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 醋酸异丙酯 、 水 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， -25.0~60.0 ℃ 、1.31 MPa 条件下， 反应 82.5h， 生成 (1S,2R,3R,4aR,6aS,7R,8R,10aR,10bR,12aR)-3-acetoxy-2-((S)-2-(dimethylamino)-2,3-dimethylbutoxy)-1,6a,8,10a-tetramethyl-8-((R)-3-methylbutan-2-yl)-6-oxo-2,3,4,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-1H-1,4a-(methanooxymethano)chrysene-7-carboxylic acid
  参考文献：
  名称：

  Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin

  摘要：

  An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.

  DOI：

  10.1021/jo300046v
• 作为产物：
  描述：

  在 sodium periodate 、 rhodium(III) chloride hydrate 作用下， 以 乙腈 为溶剂， 以1.85 kg的产率得到(S)-4-isopropyl-3,4-dimethyl-1,2,3-oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin

  摘要：

  An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.

  DOI：

  10.1021/jo300046v

文献信息

• Synthesis of Antifungal Glucan Synthase Inhibitors from Enfumafungin
  作者：Yong-Li Zhong、Donald R. Gauthier、Yao-Jun Shi、Mark McLaughlin、John Y. L. Chung、Philippe Dagneau、Benjamin Marcune、Shane W. Krska、Richard G. Ball、Robert A. Reamer、Nobuyoshi Yasuda

  DOI：10.1021/jo300046v

  日期：2012.4.6

  An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.