(2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(furan-2-yl)-3-butene | 566937-90-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(furan-2-yl)-3-butene
• 英文别名: (2R)-2-t-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(furan-2-yl)-3-butene；[(2R)-4-(furan-2-yl)-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]but-3-enyl] hexanoate
• CAS: 566937-90-4
• 化学式: C₂₀H₃₁NO₅
• 分子量: 365.47
• InChiKey: CPUJCMJNQDJKBA-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(furan-2-yl)-3-butene 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 2.17h， 生成 (4R)-4-[2-(呋喃-2-基)乙烯基]-4-甲基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.007
• 作为产物：
  描述：

  (1,3-二羟基-2-甲基-2-丙基)(2-甲基-2-丙基)氨基甲酸 在 4 A molecular sieve 、 TOYOBO 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 为溶剂， 反应 5.17h， 生成 (2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(furan-2-yl)-3-butene
  参考文献：
  名称：

  Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives

  摘要：

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.007

文献信息

• AMINO ALCOHOL DERIVATIVE OR PHOSPHONIC ACID DERIVATIVE AND MEDICINAL COMPOSITION CONTAINING THESE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1471054B1

  公开（公告）日：2009-07-01
• Asymmetric synthesis of α,α-disubstituted α-amino alcohol derivatives
  作者：Tsuyoshi Nakamura、Takashi Tsuji、Yukiko Iio、Shojiro Miyazaki、Toshiyasu Takemoto、Takahide Nishi

  DOI：10.1016/j.tetasy.2006.10.007

  日期：2006.10

  We herein report an asymmetric synthesis of alpha,alpha-disubstituted alpha-amino alcohol derivatives 3, key intermediates of a novel immunomodulator, using enzymatic desymmetrization of 2-alkyl-2-tert-butoxycarbonylamino-1,3-propanediols 1a and 1b. This method makes it possible to prepare a chiral analogue of FTY720 4. These synthetic procedures allow for a broad structure variation in order to evaluate structure-activity relationships and the mechanism of action for sphingosine 1-phosphate-1 (SIP1) receptor agonist. (c) 2006 Elsevier Ltd. All rights reserved.