[(2R,3R,4R)-3,4-dibenzoyloxy-5-oxooxolan-2-yl]methyl benzoate | 15397-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,3R,4R)-3,4-dibenzoyloxy-5-oxooxolan-2-yl]methyl benzoate
• CAS: 15397-14-5
• 化学式: C₂₆H₂₀O₈
• 分子量: 460.44
• InChiKey: PRILIIXVBXAXAU-YPAWHYETSA-N

物化性质

• 熔点：
  148 °C(Solv: acetone (67-64-1); ethanol (64-17-5))
• 沸点：
  589.9±39.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R)-3,4-dibenzoyloxy-5-oxooxolan-2-yl]methyl benzoate 在 palladium on activated charcoal 六甲基磷酰三胺 、 samarium diiodide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 [(2S,4S)-4-[(1S,2S,5R)-1-hydroxy-5-methyl-2-propan-2-ylcyclohexyl]-5-oxooxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Branched-chain carbohydrate lactones from a samarium(II) iodide-promoted serial deoxygenation-carbonyl addition reaction

  摘要：

  A new deoxygenation-carbonyl addition reaction mediated by samarium(II) iodide (SmI2) in THF/HMPA was examined with carbohydrate lactones and several substrates containing an alpha-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex optically active carbohydrate lactones appended to terpene ketones. Simple esters smoothly afforded beta-hydroxy carbonyl products. Fully benzoate-protected 3-deoxycarbohydrate lactones were reacted with simple ketones to produce C2-branched sugars. The attendant carbonyl addition to the least sterically hindered face of the aldonolactone provided the major products. Moderate diastereoselectivities (up to 5:1) were observed in the simple ketone products as determined by difference NOE studies. Finally, the terpene ketones, (-)-menthone or (+)-dihydrocarvone, were coupled to 3-deoxycarbohydrate lactones which gave C2-branched sugars with very high diastereoselectivities (up to 99:1).

  DOI：

  10.1021/jo00067a045
• 作为产物：
  描述：

  silver cyanate 、 2,3,5-tri-O-benzoyl-1-bromo-D-ribofuranosyl cyanide 以 硝基甲烷 为溶剂， 生成 [(2R,3R,4R)-3,4-dibenzoyloxy-5-oxooxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  β-呋喃呋喃糖基酰胺的立体选择性溴化。（+）-羟基龙胆素的对映选择性合成

  摘要：

  Hydantocidin是一种有效的除草天然产物，其合成通过β-D-呋喃呋喃糖基酰胺的立体选择性溴化作用而得到，仅得到α-溴β-酰胺，随后在异氰酸酯位置与氰化银进行螺环化反应，形成了乙内酰脲部分。

  DOI：

  10.1016/s0040-4039(00)77049-3

文献信息

• [EN] 4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOSIDES ET DE NUCLÉOTIDES CONTENANT DU 4-HALOGÈNE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2021137913A3

  公开（公告）日：2021-09-30
• WO2019173602A5
  申请人：——

  公开号：WO2019173602A5

  公开（公告）日：2022-03-14
• A practical synthesis of 2-deoxy aldonolactones via a SmI2-mediated α-deoxygenation reaction
  作者：Stephen Hanessian、Christian Girard、Jose Luis Chiara

  DOI：10.1016/s0040-4039(00)92313-x

  日期：1992.1

  A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.
• Enholm, Eric J.; Jiang, Shujun, Heterocycles, 1992, vol. 34, # 12, p. 2247 - 2252
  作者：Enholm, Eric J.、Jiang, Shujun

  DOI：——

  日期：——
• [EN] 4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOSIDES ET DE NUCLÉOTIDES CONTENANT DU 4'-HALOGÈNE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2022174179A9

  公开（公告）日：2023-02-02