methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside | 6991-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside
• 英文别名: methyl 2,3-O-isopropylidene-4-methylene-β-D-erythrofuranoside；(3aR,4R,6aS)-4-Methoxy-2,2-dimethyl-6-methylenetetrahydrofuro[3,4-d][1,3]dioxole；(3aS,6R,6aR)-6-methoxy-2,2-dimethyl-4-methylidene-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
• CAS: 6991-65-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VPJWQGUSNANKFC-BWZBUEFSSA-N

物化性质

• 沸点：
  241.6±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2S,3R,4R)-2,3-isopropylidenedioxy-4-methoxybutyrolactone
  参考文献：
  名称：

  Highly Substituted Cyclopentane–CMP Conjugates as Potent Sialyltransferase Inhibitors

  摘要：

  Sialylconjugates on cell surfaces are involved in many biological events such as cellular recognition, signal transduction, and immune response. It has been reported that aberrant sialylation at the nonreducing end of glycoconjugates and overexpression of sialyltransferases (STs) in cells are correlated with the malignance, invasion, and metastasis of tumors. Therefore, inhibitors of STs would provide valuable leads for the discovery of antitumor drugs. On the basis of the transition state of the enzyme-catalyzed sialylation reaction, we proposed that the cydopentane skeleton in its two puckered conformations might mimic the planar structure of the donor (CMP-Neu5Ac) in the transition state. A series of cydopentane-containing compounds were designed and synthesized by coupling different cydopentane alpha-hydroxyphosphonates with cytidine phosphoramidite. Their inhibitory activities against recombinant human ST6Gal-I were assayed, and a potent inhibitor 481 with a K-i of 0.028 +/- 0.006 mu M was identified. The results show that the cydopentanoid-type compounds could become a new type of sialyltransferase inhibitors as biological probes or drug leads.

  DOI：

  10.1021/acs.jmedchem.5b01181
• 作为产物：
  描述：

  卡培他滨杂质25 在 咪唑 、 碘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside
  参考文献：
  名称：

  [EN] NOVEL SPIROBICYCLIC ANALOGUES
  [FR] NOUVEAUX ANALOGUES SPIROBICYCLIQUES

  摘要：

  本发明涉及具有以下式（I）的新颖螺环双环类似物，其中变量的含义如权利要求中所定义。根据本发明的化合物可用作PRMT5抑制剂。本发明还涉及包括上述化合物作为活性成分的药物组合物，以及上述化合物作为药物的使用。

  公开号：

  WO2019110734A1

文献信息

• Adenosine Kinase Inhibitors. 5. Synthesis, Enzyme Inhibition, and Analgesic Activity of Diaryl-<i>erythro</i>-furanosyltubercidin Analogues
  作者：Serge H. Boyer、Bheemarao G. Ugarkar、Joel Solbach、Joseph Kopcho、Michael C. Matelich、Kristin Ollis、Jorge E. Gomez-Galeno、Rohan Mendonca、Megumi Tsuchiya、Atsushi Nagahisa、Masami Nakane、James B. Wiesner、Mark D. Erion

  DOI：10.1021/jm0503650

  日期：2005.10.1

  lyxo-furanosyltubercidin analogues as well as the newly discovered erythro-furanosyltubercidin analogues, designed to prevent 5'-O-phosphorylation and associated toxicities, were tested for their analgesic activity in the rat formalin paw model. Described herein are the synthesis, enzyme inhibition structure-activity relationships (SARs) of erythro-furanosyltubercidin analogues, and SARs of analgesic activity of various

  腺苷是一种内源性神经调节剂，当在中枢和周围神经系统中产生时，具有抗惊厥，抗炎和镇痛作用。然而，剂量限制的心血管副作用困扰着使用腺苷受体激动剂的努力。作为替代方案，我们探索了腺苷激酶抑制剂（AKIs）作为潜在的抗癫痫药的用途，并证明了在没有明显的心血管副作用的情况下腺苷受体介导的治疗作用。这些活性与以部位和事件特异性方式抑制AK导致的细胞外腺苷浓度升高有关。几种基于结核菌素的AKI，包括核糖和呋喃呋喃糖基结核病类似物，以及新近发现的赤呋喃呋喃糖基结核病类似物，旨在预防5' 在大鼠福尔马林爪模型中测试了-O-磷酸化作用和相关的毒性。在此描述的是赤型-呋喃糖基tubercidin类似物的合成，酶抑制结构-活性关系（SAR），以及各种类型的AKI的镇痛活性。还报道了AKI铅19d（GP3966）的表征，这是一种口服生物利用化合物（狗中F％= 60％），具有广谱镇痛活性（ED50 <或= 4 mg /
• Hetero-Diels–Alder additions to pent-4-enofuranosides: concise synthesis of hydroxylated pyrrolizidines
  作者：John K Gallos、Vassiliki C Sarli、Christos I Stathakis、Theocharis V Koftis、Victoria R Nachmia、Evdoxia Coutouli-Argyropoulou

  DOI：10.1016/s0040-4020(02)01251-6

  日期：2002.11

  A new facile method for the synthesis of hydroxylated pyrrolizidines of the alexine family has been developed, which involves hetero-Diels–Alder addition of ethyl 2-nitrosoacrylate to pent-4-enofuranosides and a further two-step reductive ring opening-ring closure treatment of the cycloadduct.

  已开发出一种新的简便方法来合成阿莱克辛家族的羟基化吡咯嗪核苷，该方法涉及将异亚狄尔斯-阿尔德将2-亚硝基丙烯酸乙酯添加到五-4-烯呋喃糖苷中，以及进一步的两步还原性开环开环封闭处理的加合物。
• Synthesis of [<i>n</i>,5]-Spiroketals by Ring Enlargement of Donor-Acceptor-Substituted Cyclopropane Derivatives
  作者：Christian Brand、Gesche Rauch、Michele Zanoni、Birger Dittrich、Daniel B. Werz

  DOI：10.1021/jo901902g

  日期：2009.11.20

  three-membered ring with an oxygen donor and a carbonyl acceptor group into the five-membered enol ether system. Catalytic amounts of the Lewis acid Yb(OTf)3 facilitate the ring enlargement and increase the yield of the corresponding spiroketal in many cases. When Yb(OTf)3 was used, our experiments revealed an open transition state rather than a concerted mechanism because the stereochemistry of the spirocenter

  外环烯醇醚用作合成[ n，5]-螺酮（n = 5，6）的原料。使用重氮乙酸乙酯进行金属介导的环丙烷化反应，得到带有酯基的螺环化的环丙烷衍生物。通过LiAlH 4还原相应的酯，然后使用高价碘试剂进行氧化，以中等至良好的产率产生了[ n，5]-螺缩酮。该三步骤序列中的关键步骤是将具有氧供体和羰基受体基团的三元环扩环成五元烯醇醚系统。路易斯酸Yb（OTf）3的催化量在许多情况下，可促进环的扩大并增加相应螺环的产量。当使用Yb（OTf）3时，我们的实验揭示了一个开放的过渡状态，而不是一个协调的机制，因为在扩环过程中螺中心的立体化学并不保守。结果，观察到热力学上更优选的异头[ n，5]-螺酮是主要产物。通过NOESY实验明确建立了所有结构。
• Carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides: a nitrile oxide approach
  作者：John K. Gallos、Theocharis V. Koftis

  DOI：10.1039/b007654f

  日期：——

  Nitrile oxide cycloadditions to protected enopyrano(furano)sides derived from D-glucose and D-ribose afford spiro-isoxazolines in good yield and high diastereoselectivity, which upon Raney Nickel hydrogenation in MeOH–AcOH (6∶1) undergo N–O bond cleavage followed by spontaneous aldol-like condensation to give good yields of hydroxylated six- and five-membered cyclic enaminones as the main products

  一氧化氮 衍生自受保护的依诺吡喃（呋喃）侧的环加成 d葡萄糖 和 D-核糖 可以提供高收率和高非对映选择性的螺-异恶唑啉，这在Raney Nickel上 氢化 在 甲醇-AcOH（6 ：1）进行N-O键裂解，然后自发形成类似羟醛的缩合反应，从而获得良好的羟基化六元和五元环烯胺 作为主要产品。
• Synthesis of (4S,5S)-4,5-O-isopropylidene-cyclopent-2-ene-1-one via the intramolecular Reformatsky reaction
  作者：Nadezhda A. Ivanova、Zuleykha R. Valiullina、Natal’ya P. Akhmetdinova、Mansur S. Miftakhov

  DOI：10.1016/j.tetlet.2008.08.017

  日期：2008.10

  Isomeric mixtures of bromo- and iodohydrins produced via bromohydroxylation and iodohydroxylation of exo-methylene derivative 2 undergo an intramolecular aldol cyclization–dehydration sequence under Reformatsky reaction conditions to give cyclopentenone 1.

  在exformatsky反应条件下，通过exo-亚甲基衍生物2的溴羟基化和碘羟基化生成的溴-和碘醇的异构体混合物在Reformatsky反应条件下经历分子内羟醛环化-脱水序列，得到环戊烯酮1。