2,5-dideoxy-5-iodo-3-O-(tert-butyldimethylsilyl)-D-ribonic acid-γ-lactone | 159685-39-9

• 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: 2,5-dideoxy-5-iodo-3-O-(tert-butyldimethylsilyl)-D-ribonic acid-γ-lactone
• 英文别名: (4S,5S)-4-((tert-Butyldimethylsilyl)oxy)-5-(iodomethyl)dihydrofuran-2(3H)-one；(4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-(iodomethyl)oxolan-2-one
• CAS: 159685-39-9
• 化学式: C₁₁H₂₁IO₃Si
• 分子量: 356.276
• InChiKey: IJWWEMAVYKGLBB-DTWKUNHWSA-N

物化性质

• 沸点：
  354.8±27.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dideoxy-5-iodo-3-O-(tert-butyldimethylsilyl)-D-ribonic acid-γ-lactone 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以73.2%的产率得到(3S,4R)-3-<(tert-Butyldimethylsilyl)oxy>-4-methyl-γ-butyrolactone
  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
• 作为产物：
  描述：

  (S)-N-Benzyl-N-methyl-3-acetoxy-4-pentenamide 在 咪唑 、 4-二甲氨基吡啶 、 phosphate buffer (0.1 N, pH 7) 、 碘 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 53.0h， 生成 2,5-dideoxy-5-iodo-3-O-(tert-butyldimethylsilyl)-D-ribonic acid-γ-lactone
  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

• Influence of Various Promoters on the Diastereoselectivity of Samarium(II) Iodide Mediated Reductive Carbocyclizations of ω-Iodo-α,β-unsaturated Esters Prepared from 2-Deoxy-d-ribose
  作者：Bita Samim Firouz Salari、Raphinos Kouya Biboutou、Sharon M Bennett

  DOI：10.1016/s0040-4020(00)00583-4

  日期：2000.8

  omega-Iodo-alpha,beta-unsaturated esters were reduced with SmI2 or Bu3SnH under different conditions to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 cyclizations varies with the choice of promoter, the reaction temperature, the identity of the hydroxyl protecting groups and the geometry of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-d-ribose
  作者：Sharon M. Bennett、Raphinos Kouya Biboutou、Bita Samim Firouz Salari

  DOI：10.1016/s0040-4039(98)01552-4

  日期：1998.9

  The title compounds were reduced with SmI2 or Bu3SnH to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 reductive carbocyclizations varies with the reaction conditions, the double bond geometry and with the identity of the hydroxyl protecting groups. Keywords: Alkenyl halides, carbohydrates, cyclisation, samarium and compounds.
• 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