1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose | 5432-33-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose
• 英文别名: 5-O-Carbomethoxy-1,2-O-isopropylidene-D-xylofuranose；[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl methyl carbonate
• CAS: 5432-33-7
• 化学式: C₁₀H₁₆O₇
• mdl: MFCD00015881
• 分子量: 248.233
• InChiKey: GGDOHLQEKFUTGN-ULAWRXDQSA-N

物化性质

• 沸点：
  353.7±37.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 储存条件：
  常温、避光、存放在阴凉干燥处并密封保存。

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 叠氮化锂 、 N-甲基咔唑 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 60.4h， 生成 2-Amino-9-(3'-azido-2',3'-dideoxy-beta-D-erythro-pentafuranosyl)-6-methoxy-9H-purine
  参考文献：
  名称：

  2-氨基-9-（3'-叠氮基-2'，3'-二脱氧-β-D-赤型五氟呋喃糖基）-6-甲氧基-9H-嘌呤（AzddMAP）和AzddGuo的合成

  摘要：

  描述了从1，2-O-异亚丙基-α-D-木呋喃糖开始的AzddMAP和AzddGuo的新颖合成。该合成的关键步骤涉及用甲醇代替嘌呤6位的二苯基氨基甲酰基保护基。

  DOI：

  10.1016/s0040-4039(00)93545-7
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-methoxycarbonyl-α-D-xylofuranoside 在 aluminum oxide 作用下， 以 乙醇 、 氯仿 为溶剂， 以95%的产率得到1,2-O-isopropylidene-5-O-(methoxycarbonyl)-α-D-xylofuranose
  参考文献：
  名称：

  Alkyloxycarbonyl group migration in furanosides

  摘要：

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.117

文献信息

• Some CC bond constructions on monosaccharides using cobaloxime-mediated radical alkyl-nitroalkylanion cross coupling reactions
  作者：Bruce P. Branchaud、Gui-Xue Yu

  DOI：10.1016/s0040-4039(00)79754-1

  日期：1991.7

  The formation of monosaccharide cobaloximes and their cross coupling reactions with nitroalkyl anions are demonstrated to be useful in CC bond constructions to produce branched-chain monosaccharides.

  已证明单糖钴肟的形成及其与硝基烷基阴离子的交叉偶联反应可用于CC键结构中以生产支链单糖。
• Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation
  申请人：Gilead Pharmasset LLC

  公开号：US10100076B2

  公开（公告）日：2018-10-16

  The disclosed invention is a composition for and a method of seating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  所述的发明是关于一种用于在宿主中（包括动物，特别是人类）使用一般式（I）-（XXIII）的核苷或其药用可接受的盐或前药，对Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括流感A和B）或Paramyxoviridae（包括RSV）感染，或与异常细胞增殖相关的疾病进行座位的组合物和方法。该发明还提供了一种有效的过程，用于使用实时聚合酶链反应（“RT-PCR”）在宿主中定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量。此外，该发明还揭示了可以与样本中存在的病毒量成比例发出荧光的探针分子。
• Nucleosidyl‐<i>O</i>‐Methylphosphonates: A Pool of Monomers for Modified Oligonucleotides
  作者：Dominik Rejman、Milena Masojídková、Ivan Rosenberg

  DOI：10.1081/ncn-200033912

  日期：2004.1.1

  2′‐deoxyribonucleosides, 1‐(2‐deoxy‐β‐D‐threo‐pentofuranosyl)thymine, 5′‐O‐ and 2′‐O‐phosphonomethyl derivatives of 1‐(3‐deoxy‐β‐D‐erythro‐pentofuranosyl)thymine, and 1‐(3‐deoxy‐β‐D‐threo‐pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4‐methoxy‐1‐oxido‐2‐pyridylmethyl ester group, serving also as an intramolecular

  四种天然 2'-脱氧核糖核苷、1-（2-脱氧-β-D-苏式-戊呋喃糖基）胸腺嘧啶、5'-O- 和 2' 的一组独特的 5'-O- 和 3'-O-膦酰基甲基衍生物1-(3-脱氧-β-D-赤型-戊呋喃糖基)胸腺嘧啶和1-(3-脱氧-β-D-苏式-戊呋喃糖基)胸腺嘧啶的-O-膦酰基甲基衍生物已被合成为单体库修饰寡核苷酸的合成。膦酸酯部分用 4-甲氧基-1-氧化-2-吡啶基甲酯基团保护，在偶联步骤中也作为分子内催化剂。
• Benzimidazole 2′-Isonucleosides: Design, Synthesis, and Antiviral Activity of 2-Substituted-5,6-Dichlorobenzimidazole 2′-Isonucleosides
  作者：G. A. Freeman、D. W. Selleseth、J. L. Rideout、R. J. Harvey

  DOI：10.1080/15257770008033001

  日期：2000.1

  on nucleophilic displacements of a 2'-tosylate from carbohydrate intermediates with 2-bromo-5,6-dichlorobenzidazole. 2-Bromo and 2-isopropyl amino analogs with 3'- and 5'-oxo and deoxy substitutions were prepared. The benzimidazole-2-'isonucleosides presented here demonstrated reduced activity against HCMV when compared to other D-ribofuranosyl benzimidazole analogs. In addition, they were not found

  2,5,6-三卤代苯并咪唑-β-D-呋喃核糖基核苷和2-取代的氨基5,6-二氯苯并咪唑-β-L-呋喃核糖基核苷是人巨细胞病毒（HCMV）的有效和选择性抑制剂。D-呋喃核糖基类似物在体内迅速代谢，使其不适合用作候选药物。不稳定性的主要来源被认为是异头键。介绍了一系列化学稳定的苯并咪唑-2'-异核苷的合成。所使用的合成方案基于具有2-溴-5,6-二氯苯并恶唑的碳水化合物中间体的2'-甲苯磺酸酯的亲核取代。制备了具有3'-和5'-氧代和脱氧取代的2-溴和2-异丙基氨基类似物。苯并咪唑-2-' 与其他D-呋喃呋喃糖基苯并咪唑类似物相比，此处呈现的异核苷显示出降低的抗HCMV活性。另外，未发现它们是HIV的抑制剂。
• Modified nucleosides for the treatment of viral infections and abnormal cellullar proliferation
  申请人：Stuyver Lieven

  公开号：US20110269707A1

  公开（公告）日：2011-11-03

  The disclosed invention is a composition for and a method of treating a Flaviviridae (including BVDV and HCV), Orthomyxoviridae (including Influenza A and B) or Paramyxoviridae (including RSV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans, using a nucleoside of general formula (I)-(XXIII) or its pharmaceutically acceptable salt or prodrug. This invention also provides an effective process to quantify the viral load, and in particular BVDV, HCV or West Nile Virus load, in a host, using real-time polymerase chain reaction (“RT-PCR”). Additionally, the invention discloses probe molecules that can fluoresce proportionally to the amount of virus present in a sample.

  本公开发明涉及一种用于治疗Flaviviridae（包括BVDV和HCV）、Orthomyxoviridae（包括甲型和乙型流感）或Paramyxoviridae（包括RSV）感染或与异常细胞增殖相关的条件的组合物和方法，适用于宿主，包括动物，特别是人类，使用通式（I）-（XXIII）的核苷或其药学上可接受的盐或前药。本发明还提供了一种有效的过程，用于定量病毒载量，特别是BVDV、HCV或西尼罗河病毒载量，在宿主中使用实时聚合酶链反应（“RT-PCR”）。此外，本发明还揭示了探针分子，可以与样品中存在的病毒数量成比例地发出荧光。