(R,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester | 134455-82-6

• 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: (R,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester
• 英文别名: methyl (2R)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoropropanoate
• CAS: 134455-82-6
• 化学式: C₉H₁₅FO₄
• 分子量: 206.214
• InChiKey: ASOQMYMLZXYRRD-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propionic acid methyl ester 、 (R,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester 、 sodium methylate 生成 (S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester
  参考文献：
  名称：

  OKABE, MASAMI;SUN, RUEN-CHU;ZENCHOFF, GLADYS B., J. ORG. CHEM., 56,(1991) N4, C. 4392-4397

  摘要：

  DOI：
• 作为产物：
  描述：

  (S,S*)-α-hydroxy-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester 在 乙酰胺 、 potassium fluoride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 (R,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 1-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)cytosine (F-ddC). A promising agent for the treatment of acquired immune deficiency syndrome

  摘要：

  A new and practical synthesis of a fluorinated analogue of 2',3'-dideoxycytidine (ddC), 1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine (F-ddC), is described. The key feature in the synthesis is the use of the selectively protected 2,4,5-trihydroxypentanoic acid derivative 15 as a chiral pool synthon.

  DOI：

  10.1021/jo00014a013

文献信息

• A diastereoselective synthesis of (S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester, a key intermediate for the preparation of anti-HIV effective fluorodideoxynucleosides
  作者：Maqbool A. Siddiqui、Victor E. Marquez、John S. Driscoll、Joseph J. Barchi

  DOI：10.1016/s0040-4039(00)76880-8

  日期：1994.5

  anti-HIV active 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) and 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine (2, FddC) was prepared via the diastereoselective fluorination of the chiral imide enolate obtained from 8 with N-fluorobenzenesulfonimide. The overall yield of 10 from the readily available 1,2:5,6-di-O-isopropylidene-D-mannitol was 25% (de 93%).

  （S，S）-α-氟-2,2-二甲基-1,3-二氧戊环-4-丙酸甲酯（10），是制备抗HIV活性9-（2,3-的关键中间体制备了二脱氧-2-氟-β-D-苏-戊呋喃糖基）腺嘌呤（1，FddA）和1-（2,3-二脱氧-2-氟-β-D-苏-戊呋喃糖基）胞嘧啶（2，FddC）通过由N-氟苯磺酰亚胺从8获得的手性酰亚胺烯醇的非对映选择性氟化。容易获得的1,2：5,6-二-O-异亚丙基-D-甘露糖醇的总收率为10％，为25％（de 93％）。
• Utilization of Tetrabutylammonium Triphenylsilyldifluoride as a Fluoride Source for Nucleophilic Fluorination
  作者：Anthony S. Pilcher、Herman L. Ammon、Philip DeShong

  DOI：10.1021/ja00123a025

  日期：1995.5
• OKABE, MASAMI;SUN, RUEN-CHU;ZENCHOFF, GLADYS B., J. ORG. CHEM., 56,(1991) N4, C. 4392-4397
  作者：OKABE, MASAMI、SUN, RUEN-CHU、ZENCHOFF, GLADYS B.

  DOI：——

  日期：——
• Synthesis of 1-(2,3-dideoxy-2-fluoro-.beta.-D-threo-pentofuranosyl)cytosine (F-ddC). A promising agent for the treatment of acquired immune deficiency syndrome
  作者：Masami Okabe、Ruen Chu Sun、Gladys B. Zenchoff

  DOI：10.1021/jo00014a013

  日期：1991.7

  A new and practical synthesis of a fluorinated analogue of 2',3'-dideoxycytidine (ddC), 1-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)cytosine (F-ddC), is described. The key feature in the synthesis is the use of the selectively protected 2,4,5-trihydroxypentanoic acid derivative 15 as a chiral pool synthon.