(2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-2-yl)-3-butene | 604791-90-4

• 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-(thiophen-2-yl)-3-butene
• 英文别名: (2R)-t-Butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-2-yl)-3-butene
• CAS: 604791-90-4
• 化学式: C₂₀H₃₁NO₄S
• 分子量: 381.536
• InChiKey: KPWQEXXCGFFZNS-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-2-yl)-3-butene 在 palladium on activated charcoal sodium hydroxide 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one
  参考文献：
  名称：

  Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-α-methylserinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

  摘要：

  We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.037
• 作为产物：
  描述：

  (2R)-tert-butoxycarbonylamino-3-n-hexanoyloxy-2-methyl-1-propanol 在 4 A molecular sieve 、 potassium tert-butylate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 (2R)-tert-butoxycarbonylamino-1-n-hexanoyloxy-2-methyl-4-(thiophen-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 derivatives
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20030236297A1

  公开（公告）日：2003-12-25

  Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: 1 wherein R 1 and R 2 are a hydrogen atom, an amino protecting group; R 3 is a hydrogen atom, a hydroxy protecting group; R 4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C 1 -C 10 alkylene group, a C 1 -C 10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R 5 is an aryl group; R 6 and R 7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R 5 is a hydrogen atom, Y is not a single bond or a straight chain C 1 -C 10 alkylene group.

  式（I）的化合物表现出优异的免疫抑制活性，其药理学上可接受的盐，酯或其他衍生物：其中R1和R2是氢原子，氨基保护基；R3是氢原子，羟基保护基；R4是较低的烷基基团；n是1到6之间的整数；X是乙烯基团；Y是C1-C10烷基基团，带有1到3个从取代基a和b中选择的取代基的C1-C10烷基基团；R5是芳基基团；R6和R7是氢原子，从取代基a中选择的基团；但是当R5是氢原子时，Y不是单键或直链的C1-C10烷基基团。
• AMINO ALCOHOL DERIVATIVES
  申请人：Sankyo Company, Limited

  公开号：EP1300405B1

  公开（公告）日：2007-04-18