phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside | 52544-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside
• 英文别名: [(2R,3R,4R,5S)-3,4-diacetyloxy-5-phenylsulfanyloxolan-2-yl]methyl acetate
• CAS: 52544-88-4
• 化学式: C₁₇H₂₀O₇S
• 分子量: 368.408
• InChiKey: CSENHCTYHNGBNU-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside 在 硫酸 、 氨 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 生成 [(3aR,4S,6R,6aR)-2,2-dimethyl-4-phenylsulfanyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 2-diazoacetate
  参考文献：
  名称：

  通过分子内sulf叶立德重排获得新的C-核苷内酯中间体的途径。（+）-Showdomycin的正式合成

  摘要：

  通过分子内类胡萝卜素-苯硫基呋喃糖反应制备3，6-脱水-4，5-O-异亚丙基-2-硫代苯氧基-D-卤代庚酸的内酯。

  DOI：

  10.1016/s0040-4039(00)60417-3
• 作为产物：
  描述：

  2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranose 、 benzenediazonium tetrafluoroborate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以74%的产率得到phenyl 2,3,5-tri-O-acetyl-1-thio-β-D-ribofuranoside
  参考文献：
  名称：

  在温和条件下铜 (I)-催化 Sandmeyer 型 S-芳基化 1-硫糖与芳基重氮盐

  摘要：

  在温和的反应条件下证明了通过S-芳基化从 1-硫糖制备S-芳基硫糖苷。在氯化铜 (I) 和 DBU 存在下，衍生自葡萄糖、氨基葡萄糖、半乳糖、甘露糖、核糖、麦芽糖和乳糖的多种受保护和未受保护的 1-硫糖与官能化芳基重氮盐发生交叉偶联反应。在 5 分钟内以 55-88% 的收率获得所需的产品。在标准反应条件下可以耐受各种官能团，包括卤素。证明了生物学相关的抗糖尿病药 dapagliflozin S -类似物和熊果苷S -类似物（酪氨酸酶抑制剂）的合成。

  DOI：

  10.1021/acs.joc.2c00930

文献信息

• Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI₃
  作者：Shiue-Shien Weng、Kun-Yi Hsieh、Zih-Jian Zeng

  DOI：10.1002/jccs.201600828

  日期：2017.5

  Thioglycosylation of 1‐hydroxyl glycosides catalyzed by in situ‐generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per‐modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation

  已经开发了由元素铝和分子碘原位生成的AlI 3催化的1-羟基糖苷的硫糖基化。该方法提供了另一种途径来使用异头硫醇苷，而无需使用危险的路易斯酸性活化剂或过修饰的活化硫醇源。该脱水步骤的主要优点是环境友好，操作简便，高异头非对映选择性和温和的反应条件。
• Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature
  作者：Yao Liu、Xiao-Bing Yu、Xiang-Mei Zhang、Qian Zhong、Li-Hua Liao、Nan Yan

  DOI：10.1039/d1ra04013h

  日期：——

  transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presented via arynes generated in situ combined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction

  在 TBAF( t BuOH) 4存在下，通过原位生成的芳烃与糖基硫醇结合，提出了一种温和、方便且不含过渡金属的芳基 1-硫糖苷合成方案。该方法提供了一种通用且有效的方法来制备一系列功能化的硫糖苷，并在室温下完美控制异头构型。此外，反应条件耐受多种戊糖和己糖，反应在受保护的单糖和二糖上也能顺利进行。
• Antimicrobial 2-deoxystreptamine compounds
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US06759523B2

  公开（公告）日：2004-07-06

  The present invention is directed to analogs of aminoglycoside compounds of the class having a glycosylated 2-deoxystreptamine (2-DOS) ring as well as their preparation and use as prophylactic or therapeutics against microbial infection. Compounds of the invention comprises at least one aryl, heteroaryl, substituted aryl or substituted heteroaryl group in place of a glycosyl group attached to the 2-deoxystreptamine ring.

  本发明涉及氨基糖苷类化合物的类似物，其具有糖基化的2-去氧链霉素（2-DOS）环，以及它们的制备和用作预防或治疗微生物感染的用途。本发明的化合物包括至少一个芳基、杂环芳基、取代芳基或取代杂环芳基取代2-去氧链霉素环上的糖基。
• Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron
  作者：Shiue-Shien Weng

  DOI：10.1016/j.tetlet.2009.07.077

  日期：2009.11

  A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure beta-thioglycosides were obtained in good to high yields with exclusive diastereocontrol. (C) 2009 Published by Elsevier Ltd.
• Highly Diastereoselective Thioglycosylation of Functionalized Peracetylated Glycosides Catalyzed by MoO₂Cl₂
  作者：Shiue-Shien Weng、Yow-Dzer Lin、Chien-Tien Chen

  DOI：10.1021/ol062375g

  日期：2006.11.1

  Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and beta-(1 -> 6)-S-linked-thiodisaccharide synthesis.