3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose | 68354-70-1

• 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: 3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose
• 英文别名: [(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• CAS: 68354-70-1
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ACGQAKYHAOEVJI-IGQOVBAYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose 在 吡啶 、 18-冠醚-6 、 硫酸 、 氨 、 四氯化锡 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 32.0h， 生成 9-(2-O-acetyl-5-O-benzoyl-3-O-benzyl-α-L-ribofuranosyl)-6-N-benzoyladenine
  参考文献：
  名称：

  Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides

  摘要：

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.007
• 作为产物：
  描述：

  5-O-benzoyl-1,2-O-isopropylidene-β-L-arabinofuranose 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose
  参考文献：
  名称：

  Tetrofuranose nucleoside phosphonic acids: Synthesis and properties

  摘要：

  描述了新的等电子、非同构的磷酸酯类核苷酸5'-磷酸的类似物，其磷酸基直接连接在糖环的C4'位置。这些类似物是通过从四氧杂环磷酸酯合成物和硅化的核碱基进行核苷化反应合成的。制备了具有D-和L-系列中erythro和threo构型的嘧啶化合物，并通过核磁共振谱学确定了它们的结构。核磁共振构象研究的结果显示，所有计算的构象体现出典型的核苷酸范围内的最大皱曲。在所有化合物中，S-型构象体更受青睐，并在α-D-threo-化合物中更为显著。对胸苷磷酸酶抑制的研究表明，所制备的磷酸类化合物之一是该酶的竞争性抑制剂（K_i = 4 μM）。

  DOI：

  10.1135/cccc2011038

文献信息

• The reaction of acetyliron [(η5-C5H5)Fe(CO)(PPh3)(COCH3)] with sugar aldehydes. New synthesis of deoxysugars
  作者：Zbigniew Pakulski、Aleksander Zamojski

  DOI：10.1016/0040-4020(94)00978-4

  日期：1995.1

  Aldol reactions of sugar aldehydes (5 – 13) with enolate 2 of racemic and both enantiomeric forms of acetyliron were investigated. The steric course of reactions depended strongly on the counterions used. High stereocontrol was achieved with the following cations: tin(II), diethylaluminum(I), zirconium(IV) and the triethylaluminum-containing cation. Matched pairs, particularly with the pentose- and

  糖醛（的羟醛缩合反应5 - 13）与烯醇化物2的外消旋和acetyliron的两个对映体形式进行了研究。反应的空间过程在很大程度上取决于所使用的抗衡离子。使用以下阳离子可实现高度立体控制：锡（II），二乙基铝（I），锆（IV）和含三乙基铝的阳离子。配对，特别是与戊糖和己糖衍生的醛配对，可得到具有很高立体选择性的相应的羟醛产物。醛醇缩合反应的产物在甲醇中与N-溴代琥珀酰亚胺分解。从羟醛14a-d至18a-d获得2-脱氧戊烯酸甲酯和2-脱氧己酸甲酯的立体异构体，并确定了它们的构型。乙炔铁阴离子制得的羟醛（2）和戊糖和己糖衍生的醛8 - 13解络后导致对立体异构甲基-6-脱氧的（7-脱氧） -庚（辛）糖醛。分离这些产物，并根据化学转化将其构型分配为游离的6-脱氧庚糖。在D-和L-阿拉伯糖醛（9和10）的情况下-由于产品的稳定性低-通过合成模型化合物确定构型。甲规律性是在发现1个连接耦合常数J甲基-6-脱氧hepturonates的1
• Total synthesis and antiproliferative/cytotoxic profiling of 2-epi-jaspine B
  作者：Eva Mezeiová、Miroslava Martinková、Kvetoslava Stanková、Milica Fabišíková、Jozef Gonda、Martina Pilátová、Gabriela Gönciová

  DOI：10.1016/j.carres.2016.01.011

  日期：2016.3

  whose coupling with a lipophilic segment under Wittig conditions, followed by deprotection and a THF core construction, completed the convergent synthesis of 2-epimer of 1. The final anhydrophytosphingosine 4.HCl was screened for its antiproliferative/cytotoxic activity employing multiple human cancer cell lines. In vitro evaluation revealed that 2-epi-jaspine B exhibited significant antitumour growth

  已经开发出一种直接获得2-epi-jaspine B（4.HCl）的方法。该方法的关键是使用Overman重排来安装带有氮原子的立体中心。随后的立体选择性转化的合理执行提供了功能化的支架38，其在维蒂希条件下与亲脂性片段偶联，然后脱保护并用THF核构建，完成了1的2-Epimer的聚合合成。最终的脱水植物鞘氨醇4.HCl为使用多种人类癌细胞系筛选其抗增殖/细胞毒性活性。体外评估表明，2-表-J-山脑B对所有用过的细胞均表现出显着的抗肿瘤生长抑制活性。
• Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid
  作者：Beatrice Lopez-Ortega、Sarah F. Jenkinson、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.03.030

  日期：2008.5

  The synthesis of methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribonate, a delta-2,4-cis-oxetane-azido ester scaffold derived from L-arabinose, is reported. Iterative coupling methods were utilised to form homo-oligomers up to the hexamer in order to investigate the secondary structural preferences of these systems. (C) 2008 Elsevier Ltd. All rights reserved.
• Convenient conversion of wheat hemicelluloses pentoses (d-xylose and l-arabinose) into a common intermediate
  作者：Ariane Bercier、Richard Plantier-Royon、Charles Portella

  DOI：10.1016/j.carres.2007.07.010

  日期：2007.11

  The transformation Of D-xylose and L-arabinose, the two major components of wheat straw and bran, into a unique multifunctional, optically pure, five-carbon synthon has been achieved. The synthetic sequence requires three steps: suitable protection of the hydroxyl groups of the pentoses, introduction of an iodide at the C-5 position and zinc-mediated opening of the furanose ring leading to the formation of a common substituted pent-4-enal. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and RNA-selective hybridization of α-l-ribo- and β-d-lyxo-configured oligonucleotides
  作者：Gilles Gaubert、B. Ravindra Babu、Stefan Vogel、Torsten Bryld、Birte Vester、Jesper Wengel

  DOI：10.1016/j.tet.2005.12.007

  日期：2006.3

  Three alpha-L-ribofuranosyl analogues of RNA nucleotides (alpha-L-RNA analogues) have been synthesized and incorporated into oligonucleotides using the phosphoramide approach on an automated DNA synthesizer. The 4'-C-hydroxymethyl-alpha-L-ribofuranosyl thymine monomer was furthermore synthesized. Relative to the unmodified duplexes, incorporation of a single a-L-RNA monomer into a DNA strand leads to reduced thermal stability of duplexes with DNA complements but unchanged thermal stability of duplexes with RNA complements, whereas incorporation of more than one alpha-L-RNA monomer lead to moderately decreased thermal stability also of duplexes with RNA complements. Efficient hybridization with an RNA complement and no melting transition with a DNA complement were observed with stereoregular chimeric oligonucleotides composed of a mixture of alpha-L-RNA and affinity enhancing alpha-L-LNA monomers (alpha-L-ribo-configured locked nucleic acid). Furthermore, duplexes formed between oligodeoxynucleotides containing an alpha-L-RNA monomer and complementary RNA were good substrates for Escherichia coli RNase H. RNA-selective hybridization was also achieved by the incorporation of 1-(4-C-hydroxymethyl-beta-D-lyxofuranosyl)thymine monomers into a DNA strand, whereas stable duplexes were formed with both complementary DNA and RNA when these monomers were incorporated into an RNA strand. (c) 2005 Elsevier Ltd. All rights reserved.