1,2-O-(异丙亚基)-alpha-D-呋喃木糖 5-(4-甲基苯甲酸酯) | 75096-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-O-(异丙亚基)-alpha-D-呋喃木糖 5-(4-甲基苯甲酸酯)
• 中文别名: 5-O-对甲苯甲酰基-1,2-O-异亚丙基-ALPHA-D-呋喃木糖
• 英文名称: 1,2-O-isopropylidene-5-O-(4-toluoyl)-D-xylofuranose
• 英文别名: ((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl 4-methylbenzoate；[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl 4-methylbenzoate
• CAS: 75096-60-5
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: AFHPWODMQGXJFV-QVHKTLOISA-N

物化性质

• 沸点：
  448.2±40.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-(异丙亚基)-alpha-D-呋喃木糖 5-(4-甲基苯甲酸酯) 在 吡啶 、 4-二甲氨基吡啶 、 甲酸 、 TMSTf 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis of 3′-Thioribouridine, 3′-Thioribocytidine, and Their Phosphoramidites

  摘要：

  3'-Thio-3'-deoxyribonucleosides (U and C) have been synthesized via Vorbruggen-type glycosylation with 3-S-benzoyl-5-O-toluoyl-1,2-O-diacetylfuranose, which was obtained from 1,2-O-isopropylidene-5-O-toluoyl-3-O-trifluoromethanesulfonyl-alpha-D-xylofuranose. 3'-Thio-3'-deoxyuridine has been converted to its phosphoramidite.

  DOI：

  10.1080/07328319708006225
• 作为产物：
  描述：

  alpha-D-呋喃木糖 在 硫酸 作用下， 以 吡啶 为溶剂， 反应 4.0h， 生成 1,2-O-(异丙亚基)-alpha-D-呋喃木糖 5-(4-甲基苯甲酸酯)
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162

文献信息

• Design and synthesis of HIV-1 protease inhibitors. Novel tetrahydrofuran P2/P2′-groups interacting with Asp29/30 of the HIV-1 protease. Determination of binding from X-ray crystal structure of inhibitor protease complex
  作者：Karin Oscarsson、Martina Lahmann、Jimmy Lindberg、Jussi Kangasmetsä、Torsten Unge、Stefan Oscarson、Anders Hallberg、Bertil Samuelsson

  DOI：10.1016/s0968-0896(02)00535-7

  日期：2003.3

  tested for protease inhibition and antiviral activity. Six novel 4-aminotetrahydrofuran derivatives were prepared starting from commercially available isopropylidene-alpha-D-xylofuranose yielding six symmetrical and six unsymmetrical inhibitors. Promising sub nanomolar HIV-1 protease inhibitory activities were obtained. The X-ray crystal structure of the most potent inhibitor (23, K(i) 0.25 nM) co-crystallised

  已合成了一系列具有新的四氢呋喃P2 / P2'基团的HIV-1蛋白酶抑制剂，并测试了其蛋白酶抑制作用和抗病毒活性。从市售的异亚丙基-α-D-木呋喃糖开始制备了六种新颖的4-氨基四氢呋喃衍生物，产生了六种对称和六种不对称抑制剂。获得了有希望的亚纳摩尔HIV-1蛋白酶抑制活性。讨论了与HIV-1蛋白酶共结晶的最有效抑制剂（23，K（i）0.25 nM）的X射线晶体结构，并与抑制剂1a和1b进行了比较。
• [EN] NUCLEOSIDE-THIODIPHOSPHATE-HEPTOSE COMPOUNDS FOR TREATING CONDITIONS ASSOCIATED WITH ALPK1 ACTIVITY<br/>[FR] COMPOSÉS NUCLÉOSIDE-THIODIPHOSPHATE-HEPTOSE POUR TRAITER DES AFFECTIONS ASSOCIÉES À L'ACTIVITÉ DE L'ALPK1
  申请人：PYROTECH BEIJING BIOTECHNOLOGY CO LTD

  公开号：WO2022127914A1

  公开（公告）日：2022-06-23

  The invention concerns compounds of formula (I) which modulate, especially agonize alpha kinase 1 (ALPK1) and are useful for treating a condition, disease or disorder in which a decrease or increase in ALPK1 activity contributes to the pathology or symptoms or progression of the condition, disease or disorder such as cancer, immune or inflammatory related diseases.

  本发明涉及式(I)的化合物，该化合物调节，特别是激活α激酶1(ALPK1)，并且适用于治疗某种疾病、病症或障碍，其中ALPK1活性的降低或增加会导致该疾病、病症或障碍的病理学、症状或进展，例如癌症、免疫或炎症相关疾病。
• Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-d-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction
  作者：Makoto Nomura、Tsutomu Sato、Masato Washinosu、Motoaki Tanaka、Tetsuji Asao、Satoshi Shuto、Akira Matsuda

  DOI：10.1016/s0040-4020(01)01249-2

  日期：2002.2

  A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-beta-C-ethynyl glycosyl donors in the key Vorbruggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Aminonucleosides and their Derivatives; VI¹. A New Synthesis of 1,2, 5-Tri-<i>O</i>-acyl-3-azido-3-deoxy-β-D-ribofuranose
  作者：Ainars M. Ozols、Alexey V. Azhayev、Natalia B. Dyatkina、Alexander A. Krayevsky

  DOI：10.1055/s-1980-29120

  日期：——
• Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides
  作者：Soo-Young Rhie、Wolfgang Pfleiderer

  DOI：10.1080/15257779408012162

  日期：1994.7

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.