(-)-(4S,5R)-4-acetoxy-5-acetoxymethyl-4,5-dihydrofuran-2(3H)-one | 84044-97-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(4S,5R)-4-acetoxy-5-acetoxymethyl-4,5-dihydrofuran-2(3H)-one
• 英文别名: (3S,4R)-di-O-acetyl-2-deoxy-D-ribono-1,4-lactone；(3S,4R)-3,5-diacetoxy-γ-valerolactone；3,5-O-diacetyl-2-deoxy-D-ribono-1,4-lactone；di-O-acetyl-2-deoxy-D-ribono-1,4-lactone；2-deoxyribonolactone diacetate；[(2R,3S)-3-acetyloxy-5-oxooxolan-2-yl]methyl acetate
• CAS: 84044-97-3
• 化学式: C₉H₁₂O₆
• 分子量: 216.191
• InChiKey: CORGYOATXJGQEI-JGVFFNPUSA-N

物化性质

• 沸点：
  244.3±7.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(4S,5R)-4-acetoxy-5-acetoxymethyl-4,5-dihydrofuran-2(3H)-one 生成 2-脱氧-D-核糖酰基苯胺
  参考文献：
  名称：

  KITA, YASUYUKI;TAMURA, OSAMU;ITOH, FUMIO;YASUDA, HITOSHI;KISHINO, HIROKO;+, J. ORG. CHEM., 53,(1988) N 3, 554-561

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R,4S,5R)-3,4-diacetoxy-5-acetoxymethyl-2-tetrahydrofuranone 生成 (-)-(4S,5R)-4-acetoxy-5-acetoxymethyl-4,5-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  INANAGA, JUNJI;KATSUKI, JUNKO;YAMAGUCHI, MASARU, CHEM. LETT.,(1991) N, C. 1025-1026

  摘要：

  DOI：

文献信息

• Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis – a novel transformation in carbohydrate chemistry
  作者：Markus Draskovits、Hubert Kalaus、Christian Stanetty、Marko D. Mihovilovic

  DOI：10.1039/c9cc05906g

  日期：——

  The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown

  据报道，N-杂环卡宾（NHC）催化醛糖的截留脱同位反应的发展。在还原糖的复杂情况下，可以利用NHC对醛的独特选择性。确定并机械理解了用于截留脱配或随后的氧化还原-内酯化的强底物治理的实例。更重要的是，已表明，催化剂的设计允许针对两种情况中的任何一种，调节具有结构上无偏的起始原料的反应的选择性。
• Role of Pseudoephedrine as Chiral Auxiliary in the “Acetate-Type” Aldol Reaction with Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks
  作者：Marta Ocejo、Luisa Carrillo、Jose L. Vicario、Dolores Badía、Efraim Reyes

  DOI：10.1021/jo101878j

  日期：2011.1.21

  have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected

  我们已经深入研究了在双立体分化条件下使用伪麻黄碱作为手性助剂的乙酰胺烯醇盐和手性α-杂取代醛之间的醛醇缩合反应，表明只有在匹配的试剂组合下才能实现高非对映选择性，并且前提是含α-杂原子手性醛的取代基被方便地保护。此外，所获得的高度官能化的羟醛已被用作非常有用的原料，用于立体控制制备其他令人感兴趣的化合物和手性结构单元，例如吡咯烷，吲哚并立兹，以及使用简单且高产率的致密官能化的β-羟基和β-氨基酮。方法论。
• The chemistry of O-silylated ketene acetals; diastereoselective Aldol reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes leading to 2-deoxy-D (and L)-riboses
  作者：Yasuyuki Kita、Hitoshi Yasuda、Osamu Tamura、Fumio Itoh、Yuan Ke Ya、Yasumitsu Tamura

  DOI：10.1016/s0040-4039(00)98924-x

  日期：——

  Diastereoselective carbon-carbon bond forming reaction of 2,3-O-isopropylidene-D (and L)-glyceraldehydes (D and L-2) with ketene silyl acetals (1a,b) occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxyesters (D and L-3a) as major products, which could be converted through a few additional steps to 2-deoxy-D(and L)-riboses.

  2,3-O-异亚丙基-D（和L）-甘油醛（D和L-2）与乙烯酮甲硅烷基缩醛（1a，b）的非对映选择性碳-碳键形成反应在温和的乙腈中发生，得到相应的抗-β-甲硅烷氧基酯（D和L-3a）为主要产物，可以通过一些额外的步骤将其转化为2-脱氧-D（和L）-核糖。
• Electroorganic chemistry. 76. Diastereoselective addition of electrogenerated trichloromethyl and dichloro(methoxycarbonyl)methyl anions to .alpha.-branching aldehydes
  作者：Tatsuya Shono、Naoki Kise、Takeshi Suzumoto

  DOI：10.1021/ja00313a055

  日期：1984.1
• Inanaga, Junji; Katsuki, Junko; Yamaguchi, Masaru, Chemistry Letters, 1991, # 6, p. 1025 - 1026
  作者：Inanaga, Junji、Katsuki, Junko、Yamaguchi, Masaru

  DOI：——

  日期：——