(4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone | 152442-10-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone
• 英文别名: cis-4-hydroxy-5-(iodomethyl)-4,5-dihydro-2-(3H)-furanone；(3R,4S)-3-Hydroxy-4-(iodomethyl)-γ-butyrolactone；cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanone；(4R,5S)-4-hydroxy-5-(iodomethyl)oxolan-2-one
• CAS: 152442-10-9
• 化学式: C₅H₇IO₃
• 分子量: 242.013
• InChiKey: QJIYRZUTCSEHHG-QWWZWVQMSA-N

物化性质

• 沸点：
  395.9±27.0 °C(Predicted)
• 密度：
  2.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone 在 4-二甲氨基吡啶 、 copper(I) bromide dimethylsulfide complex 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-(R)-5-pentyl-2(5H)-furanone
  参考文献：
  名称：

  Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons

  摘要：

  cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition-quenching of these butenolides under complete stereocontrol provided several polysubstituted gamma-butyrolactones including flavor components [(+)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].

  DOI：

  10.1021/jo00122a051
• 作为产物：
  描述：

  N-Benzyl-N-methyl-3-hydroxy-4-pentenamide 在 碘 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 24.0h， 生成 (4R,5R)-4,5-dihydro-4-hydroxy-5-iodomethyl-2(3H)-furanone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008

文献信息

• Synthesis of beta-L-2'-deoxy nucleosides
  申请人：Storer Richard

  公开号：US20050059632A1

  公开（公告）日：2005-03-17

  An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro- 1 -furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

  提供了一种改进的2'-改性核苷和2'-脱氧核苷的制备工艺，例如，β-L-2'-脱氧胸苷（LdT）。特别是，改进的工艺针对的是2'-脱氧核苷的合成，该合成可能使用不同的起始材料，但都通过氯糖中间体或通过2,2'-脱水-1-呋喃糖核苷中间体进行。当使用2,2'-脱水-1-呋喃糖碱基中间体时，会采用还原剂（如Red-Al）和隔离剂（如15-冠-5醚），它们能引起分子内位移反应，并形成所需核苷产品的高收率。本发明的一种替代工艺使用2,2'-脱水-1-呋喃糖碱基中间体而不使用隔离剂，也能以高收率获得2'-脱氧核苷。根据本发明制成的化合物可以作为制备其他核苷类似物的中间体，或者可以直接用作抗病毒和/或抗肿瘤剂。
• Graef, Silke; Braun, Manfred, Liebigs Annalen der Chemie, 1993, # 10, p. 1091 - 1098
  作者：Graef, Silke、Braun, Manfred

  DOI：——

  日期：——
• New entry to chiral butenolide synthons. Application to expeditious syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-trans-cognac lactone
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1016/s0040-4039(00)73129-7

  日期：1994.6

  A new envy to chiral butenolide synthons starting with iodolactonization of the readily available, homochiral N-benzyl-N-methyl-3-hydroxy-4-pentenamid (1) and its application to the syntheses of (+)-nephrosteranic acid (5), (+)-trans-whisky lactone (6), and (+)-trans-cognac lactone (7) are described.
• Functionalized chiral γ-butyrolactones as C5 building units: a straightforward formal synthesis of (+)- exo- and (+)-endo-brevicomines
  作者：Hiroki Takahata、Mami Kusunoki、Yuka Takeda、Takefumi Momose

  DOI：10.1016/0957-4166(96)00252-2

  日期：1996.7

  A straightforward formal synthesis of the insect pheromones (+)-exo-brevicomin 3 and (+)-endo-brevicomin 4 starting from homochiral functionalized gamma-butyrolactones 1 and 2 as C-5 building units is presented. Copyright (C) 1996 Published by Elsevier Science Ltd