trifluoromethanesulfonic acid (R)-1-tert-butoxymethyl-2-fluoroethyl ester | 1021943-69-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid (R)-1-tert-butoxymethyl-2-fluoroethyl ester
• 英文别名: trifluoro-methanesulfonic acid (R)-2-tert-butoxy-1-fluoromethyl-ethyl ester；[(2R)-1-fluoro-3-[(2-methylpropan-2-yl)oxy]propan-2-yl] trifluoromethanesulfonate
• CAS: 1021943-69-0
• 化学式: C₈H₁₄F₄O₄S
• 分子量: 282.256
• InChiKey: SBSQGOWSNYWRLG-LURJTMIESA-N

物化性质

• 沸点：
  248.6±40.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  醋酸叔丁酯 、 trifluoromethanesulfonic acid (R)-1-tert-butoxymethyl-2-fluoroethyl ester 在 1,3-二甲基-2-咪唑啉酮 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到tert-butyl (S)-4-(tert-butoxy)-3-(fluoromethyl)butanoate
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k
• 作为产物：
  描述：

  (S)-t-叔丁基缩水甘油醚 在 吡啶 、 氟化氢二聚体阴离子 、 四丁基硫酸氢铵 、 三乙二醇 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 trifluoromethanesulfonic acid (R)-1-tert-butoxymethyl-2-fluoroethyl ester
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k

文献信息

• PROCESS FOR THE PREPARATION OF (S)-4-FLUOROMETHYL-DIHYDRO-FURAN-2-ONE
  申请人：Zutter Ulrich

  公开号：US20080108816A1

  公开（公告）日：2008-05-08

  The present invention relates to a process of the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one of the formula by employing a dialkylmalonate of the formula wherein R 1b is lower alkyl, and the use of this process for the manufacture of DPP-IV inhibitors that are useful for the treatment and/or prophylaxis of diseases such as diabetes.

  本发明涉及一种制备(S)-4-氟甲基二氢呋喃-2-酮的方法，该方法采用式为其中R1为低级烷基的二烷基丙二酸酯，并且利用该方法制造DPP-IV抑制剂，该抑制剂可用于治疗和/或预防糖尿病等疾病。
• US7956201B2
  申请人：——

  公开号：US7956201B2

  公开（公告）日：2011-06-07
• Development of a Scalable Synthesis of (<i>S</i>)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety
  作者：Jean-Michel Adam、Joseph Foricher、Steven Hanlon、Bruno Lohri、Gérard Moine、Rudolf Schmid、Helmut Stahr、Martin Weber、Beat Wirz、Ulrich Zutter

  DOI：10.1021/op200019k

  日期：2011.5.20

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.