1-thio-β-D-glucose tetraacetate

• 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: 1-thio-β-D-glucose tetraacetate
• 英文别名: [(2S,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-sulfanyloxan-2-yl]methyl acetate
• 化学式: C₁₄H₂₀O₉S
• 分子量: 364.373
• InChiKey: SFOZKJGZNOBSHF-PDWCTOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-金刚烷乙醇 、 1-thio-β-D-glucose tetraacetate 在 1,4-Bis-(4-methylphenyl)sulfonyl-2,3,1,4-benzodithiadiazine 、 lithium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以82%的产率得到
  参考文献：
  名称：

  Polysulfuration via a Bilateral Thiamine Disulfurating Reagent

  摘要：

  An efficient moduling disulfuration was developed for polysulfide construction via a bilateral six-membered thiamine disulfurating reagent. Under the control of energy release of ring strain, diverse unsymmetrical trisulfides and tetrasulfides were generated through the assembly of nucleophiles on both sides of the sulfur-sulfur motif. This strategy exhibits features of high efficiency, mild conditions, and general scope.

  DOI：

  10.1021/acs.orglett.0c02992
• 作为产物：
  描述：

  tetra-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose 在 DL-dithiothreitol 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以3.09 g的产率得到1-thio-β-D-glucose tetraacetate
  参考文献：
  名称：

  METAL-CARBOHYDRATE COMPLEX

  摘要：

  Provided is an L-glucose derivative represented by General Formula (1) below: wherein X 1 represents a —SAuR 1 group, and X 2 , X 3 , X 4 and X 5 each independently represent an —OR 2 group, an —NH 2 group, or a fluorine atom; and R 1 represents a ligand and R 2 represents a hydrogen atom or an organic group.

  公开号：

  US20230151051A1

文献信息

• Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B ₂ pin ₂
  作者：Rongkang Wang、Fangming Chen、Lvqi Jiang、Wenbin Yi

  DOI：10.1002/adsc.202001518

  日期：2021.3.29

  arylazo sulfones were used as radical precursors for carbon‐heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and

  已经开发了一种有效的各种不对称硫醚和芳基硼酸酯的电化学合成方法。台式稳定的芳基偶氮砜被用作在电化学条件下形成碳-杂原子键的自由基前体。此外，该方法的可扩展性是通过以克为单位对芳基偶氮砜与硫醇和B 2 pin 2进行电化学巯基化和硼化来评估的。该方案不仅避免了使用化学计量的氧化剂，金属催化剂，活化剂，甚至添加了碱，而且还表现出良好的官能团耐受性。
• Synthesis and photoinitiated thiol–ene reactions of <i>exo</i>-mannals – a new route to <i>C</i>-β-<scp>d</scp>-mannosyl derivatives
  作者：János József、Nóra Debreczeni、Dániel Eszenyi、Anikó Borbás、László Juhász、László Somsák

  DOI：10.1039/d0ra07115c

  日期：——

  Syntheses of acyl protected exo-mannal derivatives were developed starting from O-peracylated mannopyranoses via the corresponding anhydro-aldose tosylhydrazones under modified Bamford–Stevens conditions. The synthesis of analogous O-peralkylated (benzylated and isopropylenated) derivatives was carried out from pyranoid and furanoid mannonolactones using methylene transfer reagents. Photoinitiated

  在改进的 Bamford-Stevens 条件下，通过相应的脱水醛糖甲苯磺酰腙，从O-过酰化的吡喃甘露糖开始合成酰基保护的外甘露醛衍生物。使用亚甲基转移试剂从吡喃类和呋喃类甘露酸内酯合成类似的O-过烷基化（苄基化和异丙基化）衍生物。这些外甘露醛的光引发硫醇-烯加成产生了相应的C- (吡喃甘露糖基/呋喃呋喃糖基)甲基硫化物，产率中等至良好，具有独特的区域选择性和 β( D ) 立体选择性。
• Stereoselective copper-catalyzed Chan–Lam–Evans N-arylation of glucosamines with arylboronic acids at room temperature
  作者：Alexandre Bruneau、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1039/c3cc44780d

  日期：——

  An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)2 and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive beta selectivity.

  已经建立了糖基胺与取代的芳基硼酸的有效且实用的N-芳基化。在室温，空气气氛下使用Cu（OAc）2和吡啶证明该方法是通用的，并且制备了各种芳基N-糖苷，具有良好的产率和优异的产率，并具有独特的β选择性。
• Anticancer Gold <i>N</i> ‐Heterocyclic Carbene Complexes: A Comparative in vitro and ex vivo Study
  作者：Natalia Estrada‐Ortiz、Federica Guarra、Inge A. M. de Graaf、Lorella Marchetti、Marina H. de Jager、Geny M. M. Groothuis、Chiara Gabbiani、Angela Casini

  DOI：10.1002/cmdc.201700316

  日期：2017.9.7

  N-heterocyclic carbene (NHC) complexes was synthesized and characterized for anticancer activity in four human cancer cell lines. The compounds' toxicity in healthy tissue was determined using precision-cut kidney slices (PCKS) as a tool to determine the potential selectivity of the gold complexes ex vivo. All evaluated compounds presented cytotoxic activity toward the cancer cells in the nano- or

  合成了一系列有机金属AuI N-杂环卡宾（NHC）配合物，并表征了其在四种人类癌细胞系中的抗癌活性。使用精密切割肾脏切片（PCKS）作为确定离体金复合物潜在选择性的工具，测定化合物在健康组织中的毒性。所有评估的化合物对纳摩尔或低微摩尔范围的癌细胞均具有细胞毒活性。带有炔基部分作为辅助配体的混合AuI NHC复合物（叔丁基乙炔基）-1,3-双-（2,6-二异丙基苯基）咪唑-2-亚基金（I）在癌细胞中显示出高细胞毒性。在体外，对健康的大鼠肾脏组织几乎没有毒性。获得的结果为癌症治疗用NHC-炔基金复合物的设计开辟了新的前景。
• Allyl-Functionalized Dioxynaphthalene[38]Crown-10 Macrocycles: Synthesis, Self-Assembly, and Thiol-ene Functionalization
  作者：Umesh Choudhary、Brian H. Northrop

  DOI：10.1002/chem.201303864

  日期：2014.1.20

  Five dioxynaphthalene[38]‐crown‐10 (DNP38C10) macrocycles bearing one, two, three, or four allyl moieties have been synthesized and their ability to spontaneously self‐assemble with methyl viologen to form [2]pseudorotaxanes has been evaluated. Association constants between methyl viologen and several of the allyl‐functionalized DNP38C10 macrocycles are found to be comparable to that of methyl viologen

  已合成了五个带有一个，两个，三个或四个烯丙基的二氧萘[38]-冠-10（DNP38C10）大环，并评估了它们与甲基紫精自组装形成[2]假轮烷的能力。发现甲基紫精和几个烯丙基官能化的DNP38C10大环之间的缔合常数与甲基紫精和未官能化的DNP38C10的缔合常数相当，但是，构成总结合自由能的焓和熵因子随烯丙基取代的增加而系统地变化。这些变化是通过对大环及其络合物的固溶相和固相分析相结合来解释的。赋予DNP38C10实用程序 烯丙基部分的大环化合物可通过硫醇-烯点击化学轻松地官能化，进一步证明了这一点。