(S)-1-(furo[2,3-c]pyridin-5-yl)ethanol | 185221-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: (S)-1-(furo[2,3-c]pyridin-5-yl)ethanol
• 英文别名: (1S)-1-furo[2,3-c]pyridin-5-ylethanol
• CAS: 185221-56-1
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: IZFJZDCDTSRECN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(furo[2,3-c]pyridin-5-yl)ethanol 以83的产率得到(R)-5-(1-chloroethyl)furo[2,3-c]pyridine
  参考文献：
  名称：

  Alpha-substituted pyrimidine-thioalkyl and alkylether compounds as

  摘要：

  本发明涉及式（I）的嘧啶-硫代烷基和烷氧基化合物以及式（IA）的嘧啶-硫代烷基和烷氧基化合物，即式（I）化合物中R.sub.4选自--H或--NR.sub.15R.sub.16的群组，其中R.sub.15为--H，R.sub.16为--H，C.sub.1-C.sub.6烷基，NH.sub.2或R.sub.15和R.sub.16一起与--N形成1-吡咯啉基，1-吗啉基或1-哌啶基；R.sub.6选自--H或卤素（优选为--Cl）的群组，总的限制是R.sub.4和R.sub.6不同时为--H。式（IA）的化合物在治疗艾滋病毒阳性的个体中是有用的，因为它们是病毒反转录酶的抑制剂。

  公开号：

  US06043248A1
• 作为产物：
  描述：

  (R)-1-(furo[2,3-c]pyridin-5-yl)ethanol 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 (S)-1-(furo[2,3-c]pyridin-5-yl)ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359

文献信息

• Stereoselective synthesis of optically active pyridyl alcohols via asymmetric transfer hydrogenation of pyridyl ketones
  作者：Kazuya Okano、Kunihiko Murata、Takao Ikariya

  DOI：10.1016/s0040-4039(00)01695-6

  日期：2000.11

  A chiral Ru(II) complex, RuCl[(S,S)-N-(p-toluenesulfonyl)-1,2-diphenyl-ethylenediamine](p-cymene), serves as an efficient catalyst for asymmetric transfer hydrogenation of 2-acetylpyridine with a substrate to catalyst molar ratio of 200–1000 with HCOOH as a hydrogen source to give (S)-1-(2-pyridyl)ethanol in an almost quantitative yield and with 95% ee.

  手性Ru（II）配合物RuCl [（S，S）-N-（对甲苯磺酰基）-1,2-二苯基-乙二胺]（对甲基苯甲基）可作为有效的催化剂，用于2-的不对称转移加氢以HCOOH为氢源的底物与催化剂的摩尔比为200-1000的乙酰基吡啶，以几乎定量的产率得到95％ee的（S）-1-（2-吡啶基）乙醇。
• Microbial Enantioselective Reduction of Acetylpyridine Derivatives
  作者：Shigeru KAWANO、Miho HORIKAWA、Yoshihiko YASOHARA、Junzo HASEGAWA

  DOI：10.1271/bbb.67.809

  日期：2003.1

  The microbial enantioselective reduction of acetylpyridine derivatives was studied. Many microorganisms were found to reduce 5-acetylfuro[2,3-c]pyridine (AFP) to (S)-5-(1-hydroxyethyl)furo[2,3-c]-pyridine (FPH). Candida maris IFO10003 reduced AFP to (R)-FPH with high enantioselectivity. The microbial reduction reaction was optimized. The aeration conditions and glucose concentration affected the yield

  研究了乙酰吡啶衍生物的微生物对映选择性还原。发现许多微生物将5-乙酰基呋喃[2,3-c]吡啶（AFP）还原为（S）-5-（1-羟乙基）呋喃[2,3-c]-吡啶（FPH）。玛丽假丝酵母IFO10003将AFP还原为对映选择性高的（R）-FPH。优化了微生物还原反应。曝气条件和葡萄糖浓度影响产量和立体选择性。细胞积聚了17.5 g / l（107 mM）的（R）-FPH，产率为99％，对映体过量（ee）为97％。马里氏梭菌的无细胞提取物积累了91.5 g / l（559 mM），具有超过99％ee的酶促NADH再生。（R）-FPH是合成HIV逆转录酶抑制剂的重要中间体，
• Process for producing optically active pyridineethanol derivatives
  申请人：Kaneka Corporation

  公开号：US20040043460A1

  公开（公告）日：2004-03-04

  The present invention relates to a method of producing an optically active pyridineethanol derivative. More particularly, it relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing an enzyme or enzyme source to act on polycyclic acetylpyridine derivatives. The present invention also relates to a novel enzyme which can be used in the production method mentioned above, a DNA coding for said enzyme, a recombinant vector having said DNA, and a transformant having said recombinant vector. The invention further relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing the above novel enzyme or the above transformant to act on optically inactive polycyclic pyridineethanol derivatives.

  本发明涉及一种制备光学活性吡啶乙醇衍生物的方法。更具体地说，它涉及通过使酶或酶源作用于多环乙酰吡啶衍生物来制备光学活性多环吡啶乙醇衍生物的方法。本发明还涉及一种新的酶，可用于上述制备方法，以及编码该酶的DNA，具有该DNA的重组载体和具有该重组载体的转化体。本发明还涉及一种通过使上述新酶或上述转化体作用于光学不活性多环吡啶乙醇衍生物来制备光学活性多环吡啶乙醇衍生物的方法。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE PYRIDINEETHANOL DERIVATIVES
  申请人：KANEKA CORPORATION

  公开号：EP1116795A1

  公开（公告）日：2001-07-18

  The present invention relates to a method of producing an optically active pyridineethanol derivative. More particularly, it relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing an enzyme or enzyme source to act on polycyclic acetylpyridine derivatives. The present invention also relates to a novel enzyme which can be used in the production method mentioned above, a DNA coding for said enzyme, a recombinant vector having said DNA, and a transformant having said recombinant vector. The invention further relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing the above novel enzyme or the above transformant to act on optically inactive polycyclic pyridineethanol derivatives.

  本发明涉及一种生产光学活性吡啶乙醇衍生物的方法。更具体地说，它涉及一种通过使酶或酶源作用于多环乙酰基吡啶衍生物来生产光学活性多环吡啶乙醇衍生物的方法。 本发明还涉及一种可用于上述生产方法的新型酶、编码所述酶的 DNA、具有所述 DNA 的重组载体以及具有所述重组载体的转化体。 本发明还涉及一种生产光学活性多环吡啶乙醇衍生物的方法，其方法是使上述新型酶或上述转化体作用于光学无活性的多环吡啶乙醇衍生物。
• Optical resolution of (±)-1-furo[2,3-c]pyridin-5-yl-ethanol using extraction technique: formal total synthesis of PNU-142721, HIV-1 reverse transcriptase inhibitor
  作者：Masato Matsugi、Kinuyo Itoh、Masatomo Nojima、Yuri Hagimoto、Yasuyuki Kita

  DOI：10.1016/s0040-4039(03)00612-9

  日期：2003.4

  A formal total synthesis of PNU-142721 was effectively carried out to prepare the chiral non-racemic synthon 1-furo[2,3-c]pyridin-5-yl-ethanol. It was easily obtained utilizing the optical resolution of the corresponding diastereomeric derivatives derived from 3beta-acetoxyetienic acid by using the extraction technique. (C) 2003 Elsevier Science Ltd. All rights reserved.