3,6-anhydro-2-deoxy-D-arabino-hexono-1,4-lactone | 129151-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 3,6-anhydro-2-deoxy-D-arabino-hexono-1,4-lactone
• 英文别名: (1R,5R,8R)-8-hydroxy-2,6-dioxabicyclo[3.3.0]octan-3-one；(3R,3aR,6aR)-3-hydroxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-5-one
• CAS: 129151-47-9
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: PVUSTORUMVYQDK-ZMIZWQJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-2-deoxy-D-arabino-hexono-1,4-lactone 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 18.0h， 以55%的产率得到3,6-anhydro-2-deoxy-5-O-tosyl-D-arabino-hexono-1,4-lactone
  参考文献：
  名称：

  Vitamin C and isovitamin C derived chemistry. 4. Synthesis of some novel furanone chirons

  摘要：

  DOI：

  10.1021/jo00306a008
• 作为产物：
  描述：

  L-古洛糖酸-gamma-内酯 在 palladium on activated charcoal 氢溴酸 、 氢气 、 溶剂黄146 、 三乙胺 、 silver(l) oxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 30.0 ℃ 、266.64 Pa 条件下， 反应 11.5h， 生成 3,6-anhydro-2-deoxy-D-arabino-hexono-1,4-lactone
  参考文献：
  名称：

  Vitamin C and isovitamin C derived chemistry. 4. Synthesis of some novel furanone chirons

  摘要：

  DOI：

  10.1021/jo00306a008

文献信息

• Synthesis of 3,5-Anhydro-2-deoxy-1,4-glyconolactones by Palladium(II)-Catalyzed, Regioselective Oxycarbonylation of C₅- and C₆-Enitols. ω-Homologation of Aldoses to Produce Intermediates for<i>C</i>-Glycoside/<i>C</i>-Nucleoside Synthesis
  作者：Tibor Gracza、Thomas Hasenöhrl、Ulrich Stahl、Volker Jäger

  DOI：10.1055/s-1991-28400

  日期：——

  The palladium(II)-catalyzed oxycarbonylation, known with alkenols and alkenediols, is studied with optically active 4-pentenitols (-triols) 1, 7 and 5-hexenitols (-tetrols) 12, 15, 18. Efficient routes for the substrates are provided, mostly from carbohydrate precursors. In all cases, bicyclic 3,6-anhydro-2-deoxy-1, 4-glyconolactones, versatile intermediates of C-glycosidic structure, are isolated with high selectivity and in good yield (53-77%). Several minor products (4-14% of regio-/diastereoisomers) from two competing pathways are observed and identified. The oxycarbonylation of alkenitols thus completes a novel sequence that transforms aldoses into homologous anhydro-glyconolactones, by C1-elongation at the terminal site. In the key step, the 3,4-threo arrangement is produced, from each of the four diastereomeric alkenitols studied (of the 6 cases available in the C5 and C6 series). The stereochemical protocol is summarized, e.g., by the transition D-gluco (aldose) → D-xylo (hexenitol, 15) → L-ido (anhydro-deoxyheptenolactone 26), as demonstrated.

  使用钯(II)催化氧羰基化己烯醇和烯二醇已知的方法，研究了光学活性的4-戊烯氮醇（三醇）1、7和5-己烯氮醇（四醇）12、15、18。提供了一种高效的路径，大部分以碳水化合物为底物。在所有情况下,双环3,6-脱水-2-脱氧-1,4-甘露环酮,C-糖苷结构的多种中间体,均以高选择性和较好的产率被分离出来(53-77%)。观察和识别了来自两个竞争途径的数个次要产品(4-14%的位/对映异构体)。烯氮醇的氧羰基化完成了一个将醛糖转化为同源脱水甘露醇环酮的新序列,通过在末端位点的C1延伸。在关键步骤中，从所研究的四种差向异构的烯醇(C5和C6系列共有6个)中，每个都产生了3,4-苏型排列。例如，通过D-葡萄糖(醛糖) → D-木糖(己烯醇,15) → L-艾杜糖(脱氧庚烯环酮26)这样的过渡，来证明立体化学的规程。
• Continuous Pd-Catalyzed Carbonylative Cyclization Using Iron Pentacarbonyl as a CO Source
  作者：Pavol Lopatka、Martin Markovič、Peter Koóš、Steven V. Ley、Tibor Gracza

  DOI：10.1021/acs.joc.9b02453

  日期：2019.11.15

  continuous flow carbonylation reaction using iron pentacarbonyl as source of CO. The described transformation using this surrogate was designed for use in commonly accessible flow equipment. Optimized conditions were applied to a scalable synthesis of the natural compound isolated from perianal glandular pheromone secretion of the African civet cat. In addition, a flow Pd-catalyzed carbonylation of aryl

  该工作公开了使用五羰基铁作为CO源的连续流动羰基化反应。使用该替代物描述的转化设计用于通常可使用的流动设备中。将优化的条件应用于从非洲麝猫的肛周腺信息素分泌物中分离的天然化合物的可扩展合成。另外，成功地报道了流式钯催化的芳基卤化物的羰基化反应。
• Homogeneous Cyclocarbonylation of Alkenols with Iron Pentacarbonyl
  作者：Matej Babjak、Martin Markovič、Beáta Kandríková、Tibor Gracza

  DOI：10.1055/s-0033-1340619

  日期：——

  times but comparable yields and selectivity. We report substantially improved reaction conditions for palladium(II)-catalyzed tandem cyclization–intramolecular oxycarbonylation of (amino)polyols with a terminal double bond, based on utilization of iron pentacarbonyl [Fe(CO)5] as an affordable and safe liquid supply of the carbonyl unit fully replacing gaseous carbon monoxide. Direct comparison with the

  摘要 我们报告了基于五羰基铁[Fe（CO）5 ]的可负担且安全的液体供应，基于钯（II）催化的串联环化反应-具有末端双键的（氨基）多元醇的分子内氧羰基化大大改善了反应条件羰基单元完全取代气态一氧化碳。在一系列先前公开的底物上与经典版本的直接比较表明，反应时间总是较短，但产率和选择性却相当。 我们报告了基于五羰基铁[Fe（CO）5 ]的可负担且安全的液体供应，基于钯（II）催化的串联环化反应-具有末端双键的（氨基）多元醇的分子内氧羰基化大大改善了反应条件羰基单元完全取代气态一氧化碳。在一系列先前公开的底物上与经典版本的直接比较表明，反应时间总是较短，但产率和选择性却相当。
• A Short Asymmetric Synthesis of Sauropunols A–D
  作者：Tibor Gracza、Martin Markovič、Peter Koóš

  DOI：10.1055/s-0036-1588999

  日期：2017.7

  Abstract A short and efficient asymmetric synthesis of natural sauropunols A, B, and C/D has been accomplished in 6 steps from divinylcarbinol with overall yield of 19%, 7% and 32%, respectively. The key synthetic steps include effective Sharpless asymmetric epoxidation of penta-1,4-dien-3-ol and a highly diastereoselective Pd-catalysed oxycarbonylation of pentene-1,2,3-triol. The structures of sauropunols

  摘要 从二乙烯基甲醇中分六步完成了天然sauropunols A，B和C / D的短而有效的不对称合成，总收率分别为19％，7％和32％。关键的合成步骤包括有效地进行penta-1,4-dien-3-ol的Sharpless不对称环氧化和戊二烯1,2,3-三醇的高度非对映选择性Pd催化的羰基化。已证实sauropunols A和B的结构。 从二乙烯基甲醇中分六步完成了天然sauropunols A，B和C / D的短而有效的不对称合成，总收率分别为19％，7％和32％。关键的合成步骤包括有效地进行penta-1,4-dien-3-ol的Sharpless不对称环氧化和戊二烯1,2,3-三醇的高度非对映选择性Pd催化的羰基化。已证实sauropunols A和B的结构。 本文的主要数据可在http://www.thieme-connect.com/ejournals/toc/synthesi
• Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors
  作者：Inge Lundt、Holger Frank

  DOI：10.1016/s0040-4020(01)89337-6

  日期：1994.1

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.