(S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester | 134455-81-5

• 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: (S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester
• 英文别名: methyl (2S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-fluoropropanoate
• CAS: 134455-81-5
• 化学式: C₉H₁₅FO₄
• 分子量: 206.214
• InChiKey: ASOQMYMLZXYRRD-BQBZGAKWSA-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：

  (S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester 、 盐酸 生成 (3S,5S)-3-fluoro-5-(hydroxymethyl)oxolan-2-one
  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：

  (R)-2-Acetoxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid methyl ester 在 二乙胺基三氟化硫 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S,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％）。
• US5498719A
  申请人：——

  公开号：US5498719A

  公开（公告）日：1996-03-12
• [EN] PROCESSES FOR PREPARING 2-DIHALO RIBOLACTONES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE 2-DIHALO-RIBOLACTONES
  申请人：COCRYSTAL PHARMA INC

  公开号：WO2017075590A2

  公开（公告）日：2017-05-04

  Methods for forming 2-bromo, 2-fluoro ribofuranose intermediates and 2-chloro, 2- fluoro ribofuranose intermediates for use in preparing antiviral nucleosides are disclosed. Methods for forming nucleosides, and nucleoside prodrugs, using the intermediates, are also disclosed. The methods all produce intermediates, and the resulting nucleosides and prodrugs thereof, wherein the chirality of the carbon at the 2-position is controlled. In some embodiments, the chemistry involves using chiral auxiliaries, such as (R)-2,2-dimethyl-l,3- dioxolane-4-carbaldehyde, and in other embodiments, the chemistry involves using chiral starting materials, such as D-xylose.