5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone | 129151-46-8

• 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: 5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone
• 英文别名: (S)-5-((R)-oxiran-2-yl)dihydrofuran-2(3H)-one；(5S)-5-[(2R)-oxiran-2-yl]oxolan-2-one
• CAS: 129151-46-8
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: ZHSREEZDXFCRLR-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-2,3-dideoxy-D-erythro-hexono-1,4-lactone 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 三苯基氢化锡 、 氢气 、 三乙胺 、 lithium chloride 、 copper dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~110.0 ℃ 、101.33 kPa 条件下， 反应 30.83h， 生成 (2R,4S,5S)-2-(2-propyl)-4-hydroxy-5-<(tert-butyloxycarbonyl)amino>-7-methyloctanoic acid δ-lactone
  参考文献：
  名称：

  On a Possible Neutral Charge State for the Catalytic Dyad in β-Secretase When Bound to Hydroxyethylene Transition State Analogue Inhibitors

  摘要：

  beta-Secretase is one of the aspartic proteases involved in the formation of amyloid plaques in Alzheimer's disease patients Our previous results using a combination of surface plasmon resonance experiments with molecular Modeling calculations: suggested that the Asp dyad in beta-secretase bound to hydroxylethylene containing inhibitors adopts a neutral charged state. In this work, we show that the Asp dyad diprotonated state reproduced the binding ranking of a set of these inhibitors better than alternative protonation states.

  DOI：

  10.1021/jm101568y
• 作为产物：
  描述：

  5,6-anhydro-2,3-dideoxy-D-erythro-hex-2-enono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以87%的产率得到5,6-anhydro-2,3-dideoxy-D-erythro-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

• Preparation of Enantiomerically Pure Mono- and Diepoxylactones from Aldonolactones
  作者：Inge Lundt、Christian Pedersen

  DOI：10.1055/s-1992-26196

  日期：——

  Treatment of bromodeoxyaldonolactones with a nonaqueous base, such as potassium fluoride, caesium fluoride or potassium carbonate in acetone, yields 2,3-anhydro-, 5,6-anhydro-, and 2,3: 5,6-dianhydrohexonolactones, or 2,3-anhydro-and 2,3:6,7-dianhydrohepto-nolactones in good yields.

  用非水基（如丙酮中的氟化钾、氟化铯或碳酸钾）处理溴代脱氧己内酯，可得到 2,3-脱水、5,6-脱水和 2,3：5,6-二氢己内酯或 2,3-脱水-2,3:6,7-二氢七内酯，收率良好。
• Synthesis and potential antidiabetic and lipid-lowering activities of putative asperidine B and its desmethyl analogue
  作者：Kittisak Thongpat、Pannita Holasut、Atcharaporn Ontawong、Jakkapong Inchai、Acharaporn Duangjai、Vatcharin Rukachaisirikul、Chutima S. Vaddhanaphuti、Kwanruthai Tadpetch

  DOI：10.1016/j.bmcl.2023.129437

  日期：2023.9

  pyrrolidin-3-ol alkaloid. This work reports the first enantioselective synthesis of putative asperidine B and its desmethyl analogue via a chiron approach starting from d-isoascorbic acid as well as evaluation of their free-radical scavenging, antidiabetic, and anti-hyperlipidemic activities. Both putative asperidine B and its desmethyl analogue markedly reduced the total reactive oxygen species (ROS) without

  推定的 asperidine B 是一种非天然 2,6-二取代哌啶-3-醇，是 (+)-preussin（一种著名的吡咯烷-3-醇生物碱）的结构异构体。这项工作报告了从d-异抗坏血酸出发，通过 Chiron 方法首次对映选择性合成推定的阿哌啶 B 及其去甲基类似物，并评估了它们的自由基清除、抗糖尿病和抗高血脂活性。推定的阿哌啶 B 及其去甲基类似物均显着降低了肝细胞癌细胞 (HepG2) 中的总活性氧 (ROS)，且没有细胞毒性。去甲基类似物是两种抗氧化剂基因表达（谷胱甘肽过氧化物酶和超氧化物歧化酶）的有效诱导剂，而推定的阿哌啶 B 仅诱导超氧化物歧化酶。此外，推定的阿哌啶 B 通过 α-葡萄糖苷酶抑制发挥有效的抗糖尿病活性 (IC 50  = 0.143 ± 0.001 mg/mL)，与抗糖尿病药物阿卡波糖相当。与母体 asperidine B (preussin) 一致，推定的 asperidine
• Juennemann, Josef; Lundt, Inge; Thiem, Joachim, Acta Chemica Scandinavica, 1994, vol. 48, # 3, p. 265 - 268
  作者：Juennemann, Josef、Lundt, Inge、Thiem, Joachim

  DOI：——

  日期：——
• Regioselective opening of epoxyaldonolactones to fluorodeoxyaldonolactones using Tetrabutylammonium dihydrogentrifluoride
  作者：Inge Lundt、Domenico Albanese、Dario Landini、Michele Penso

  DOI：10.1016/s0040-4020(01)87207-0

  日期：1993.8

  A study on the hydrofluorination of epoxyaldonolactones with Bu4N+H2F3- (1) under solid-liquid PTC and homogeneous conditions has been performed. Unsubstituted 5,6-epoxy-hexono-1,4-lactones 2a give the corresponding fluorohydrins in high yield using catalytic amounts of 1 and an excess of solid KHF2, while an equimolar amount of 1 is used with 2,3-epoxyaldonolactones 2d-g and 5,6-epoxy-hexono-1,4-lactones containing a free hydroxy group 2b,c. In all cases the reaction is completely regio- and stereoselective affording 6-deoxy-6-fluoro-hexonolactones 3a,b and 2-deoxy-2-fluoro-aldonolactones 3d,f.
• VEKEMANS, JOZEF A. J. M.;DAPPERENS, CORNELIS W. M.;CLAESSEN, RON;KOTEN, A+, J. ORG. CHEM., 55,(1990) N9, C. 5336-5344
  作者：VEKEMANS, JOZEF A. J. M.、DAPPERENS, CORNELIS W. M.、CLAESSEN, RON、KOTEN, A+

  DOI：——

  日期：——