(2-iodoethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 16977-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-iodoethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-iodoethoxy)oxan-2-yl]methyl acetate
• CAS: 16977-79-0
• 化学式: C₁₆H₂₃IO₁₀
• 分子量: 502.257
• InChiKey: GHUHKLKAXBLEAS-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2-iodoethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-叠氮乙基-2,3,4,6-四-O-乙酰-β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  3-(2,6-双(三氟甲基)苯氧基)-6-(prop-2-yn-1-yloxy)邻苯二甲腈的合成、点击反应、分子结构、光谱和DFT计算研究

  摘要：

  摘要 化合物 3-(2,6-双(三氟甲基)苯氧基)-6-(prop-2-yn-1-yloxy)phthalonitrile 已被合成并通过不同的表征技术如元素分析、IR、UV-vis光谱和 X 射线单晶测定。使用 Hartree-Fock (HF) 和密度泛函理论 (DFT) 与 6-31G(d) 基组比较了该化合物在基态的 X 射线测定的分子几何结构。该化合物通过点击反应与糖叠氮化物反应形成三唑环。碳水化合物分子和氟化有机化合物之间的协同作用实现了新的合成途径、性质和化学科学中的应用。.

  DOI：

  10.1016/j.molstruc.2016.01.078
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 (2-iodoethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  单核苷酸SATE葡萄糖基硫代磷酸酯是一系列新的前核苷酸。

  摘要：

  带有S-新戊酰基-2-硫代乙基（tBuSATE）基团和与磷原子通过2-结合的葡糖基残基的3'-叠氮基-2'，3'-二脱氧胸苷（AZT）的两种硫代磷酸酯衍生物的合成和研究报道了氧乙基连接。这些衍生物可以被认为是新系列核苷酸前药（前核苷酸）的原型。

  DOI：

  10.1081/ncn-120022681

文献信息

• A Cyclic Sugar Unit Interacts More Strongly with DNA Than Do Open-Chain Polyol Counterparts in Sugar-Linked Synthetic DNA Intercalators
  作者：Atsushi Kumasaki、Tomoko Goto、Shigeo Nakamura、Toshihiro Ihara、Makoto Takagi

  DOI：10.1246/cl.2001.370

  日期：2001.4

  We synthesized new DNA intercalators, polyol- or cyclic sugar-linked anthraquinone derivatives. The binding affinity of these DNA intercalators is suggested to be controlled by the configuration and steric structure of sugar chain with the cyclic sugar chain interacting more strongly than the open-chain polyol unit with double stranded DNA.

  我们合成了新的 DNA 中间体--多元醇或环糖连接的蒽醌衍生物。这些 DNA 中间体的结合亲和力受糖链的构型和立体结构控制，环糖链比开链多元醇单元与双链 DNA 的相互作用更强。
• Syntheses and photodynamic properties of glucopyranoside-conjugated indium(III) porphyrins as a bifunctional agent
  作者：Misaki Nakai、Tomohiro Maeda、Tsuyoshi Mashima、Shigenobu Yano、Shiho Sakuma、Eriko Otake、Akimichi Morita、Yasuo Nakabayashi

  DOI：10.1142/s1088424613500934

  日期：2013.12

  The glucopyranoside-conjugated porphyrins, H ₂ TPP p- O -( CH ₂)₂- O - OAcGlc } (1), [ InTPP p- O -( CH ₂)₂- O - OAcGlc }] NO ₃ (2), H ₂ TPP p- O -( CH ₂)₂- O - Glc } (3), [ InTPP p- O -( CH ₂)₂- O - Glc ]- NO ₃ (4) and ZnTPP p- O -( CH ₂)₂- O - OAcGlc } (5) were synthesized, and characterized by ¹ H NMR, ¹³ C NMR, ESI-MS, UV-vis spectroscopies and elemental analyses. In the ¹ H NMR spectrum of 2, two sets of signals were observed for H -atoms of the phenyl group of porphyrin, indicating that 2 has the axial chirality due to a NO ₃ ion coordinating to the indium atom. Abilities of the singlet oxygen production of these porphyrins, investigated by using 1,3-diphenylisobenzofuran (DPBF) as a quencher, were higher than those of the free-based and zinc porphyrins, reflecting the heavy atom effect. The photodynamic properties of these porphyrin derivatives were investigated against COLO 679. All of the glucopyranoside-conjugated porphyrins exhibited the high photocytotoxicity compared with Laserphyrin^®. Above all, 4 exhibited the highest photocytotoxicity, coinciding with the high abilities of this complex for the singlet oxygen production and the cell permeability.

  (1), [ InTPP p- O -( CH 2)2- O - OAcGlc }] NO 3 (2), H 2 TPP p- O -( CH 2)2- O - Glc } (3), [ InTPP p- O -( CH 2)2- O - OAcGlc }] NO 3(3), [ InTPP p- O -( CH 2)2- O - Glc ]- NO 3 (4) and ZnTPP p- O -( CH 2)2- O - OAcGlc } (5) were synthesed.(5) 的合成，并通过 1 H NMR、13 C NMR、ESI-MS、UV-vis 光谱和元素分析对其进行了表征。在 2 的 1 H NMR 光谱中，卟啉苯基的 H 原子出现了两组信号，表明 2 具有轴向手性，这是由于 NO 3 离子与铟原子配位所致。通过使用 1,3-二苯基异苯并呋喃（DPBF）作为淬灭剂，研究发现这些卟啉产生单线态氧的能力高于游离基卟啉和锌卟啉，这反映了重原子效应。研究了这些卟啉衍生物对 COLO 679 的光动力特性。与 Laserphyrin® 相比，所有葡萄糖吡喃糖苷共轭卟啉都表现出较高的光细胞毒性。其中，4 号卟啉的光毒性最高，这与该复合物产生单线态氧和细胞渗透性的能力很强不谋而合。
• S-Trityl protection of bis-amino bis-thiol (BAT) chelator enables flexible derivatisation and facile labelling with technetium-99m
  作者：Bernard J. Cleynhens、Guy M. Bormans、Hubert P. Vanbilloen、Dominique V. Vanderghinste、Davy M. Kieffer、Tjibbe J. de Groot、Alfons M. Verbruggen

  DOI：10.1016/s0040-4039(03)00224-7

  日期：2003.3

  We have coupled S,S'-bis-trityl N-BOC protected 1,2-ethylenedicysteamine, a bis-amino bis-thiol (BAT) tetraligand, via a propylene or ethylene spacer to several biologically active molecules including 2-nitroimidazole, desethylflumazenil, a beta-CIT analogue, glucose and 2-(2'-hydroxy-4'-aminophenyl)-1,3-benzothiazole. The conjugates were efficiently labelled with technetium-99m by consecutive heating of the S,S'-bis-trityl protected ligand in hydrochloric acid followed by neutralisation and heating in the presence of Tc-99m-tartrate. The S,S'-bis-trityl BAT chelator is an interesting synthon that allows both flexible derivatisation with various biologically active molecules and facile labelling with technetium-99m. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Helferich; Lutzmann, Justus Liebigs Annalen der Chemie, 1939, vol. 541, p. 1,10
  作者：Helferich、Lutzmann

  DOI：——

  日期：——
• Biolabile constructs for pronucleotide design
  作者：Anne Jochum、Nathalie Schlienger、David Egron、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1016/j.jorganchem.2004.11.015

  日期：2005.5

  After summarising the in vitro and in vivo results obtained with nucleotide prodrugs (pronucleotides) bearing two S-acyl-2-thioethyl (SATE) groups as esterase-labile phosphate protections, we will describe recent work on mononucleoside mixed phosphoester derivatives. These new series of biolabile constructs were designed to lead to the selective intracellular delivery of the corresponding 5'-mononucleotide through different enzyme-mediated activation steps. (c) 2004 Elsevier B.V. All rights reserved.