methyl 4-thio-α-D-galactopyranoside | 118868-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-thio-α-D-galactopyranoside
• 英文别名: 4-thio-α-D-galactopyranoside；(2S,3R,4R,5R,6R)-6-(hydroxymethyl)-2-methoxy-5-sulfanyloxane-3,4-diol
• CAS: 118868-81-8
• 化学式: C₇H₁₄O₅S
• 分子量: 210.251
• InChiKey: PFROTWRHYMLGHR-OVHBTUCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-thio-α-D-galactopyranoside 在 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 49.0h， 生成 4-thio-α/β-D-galactofuranose
  参考文献：
  名称：

  A convenient synthesis of 4-thio-D-galactofuranose

  摘要：

  DOI：

  10.1021/jo00269a025
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside 在 吡啶 、 sodium methylate 、 potassium thioacyanate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 70.0h， 生成 methyl 4-thio-α-D-galactopyranoside
  参考文献：
  名称：

  A convenient synthesis of 4-thio-D-galactofuranose

  摘要：

  DOI：

  10.1021/jo00269a025

文献信息

• Streamlined Iterative Assembly of Thio‐Oligosaccharides by Aqueous <i>S</i> ‐Glycosylation of Diverse Deoxythio Sugars
  作者：Peng Wen、Peijing Jia、Qiuhua Fan、Bethany J. McCarty、Weiping Tang

  DOI：10.1002/cssc.202102483

  日期：2022.2.8

  Step by step: A streamlined practical iterative synthesis of S-oligosaccharides is developed in aqueous solution without the need of protecting any of the hydroxy groups. Various deoxythio sugar building blocks can be prepared efficiently. The Ca(OH)2-promoted aqueous S-glycosylation can be realized with high chemo- and stereoselectivity.

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。
• Synthesis of Deoxyglycosides by Desulfurization under UV Light
  作者：Jian-Tao Ge、Ying-Ying Li、Jun Tian、Rong-Zhen Liao、Hai Dong

  DOI：10.1021/acs.joc.7b00896

  日期：2017.7.7

  performed to develop a highly efficient method whereby desulfurization could be completed in 0.5 h under ultraviolet light, at room temperature, and in the presence of trialkylphosphine. Using this method, deoxyglycosides could be produced from sulfur-containing glycosides in almost quantitative yields. The much higher reactivity of desulfurization with triethylphosphine versus that with triethylphosphite

  进行这项研究是为了开发一种高效的方法，该方法可以在紫外线，室温，三烷基膦的存在下于0.5小时内完成脱硫。使用这种方法，可以几乎定量地从含硫糖苷生产脱氧糖苷。还讨论了用三乙基膦进行脱硫的反应性比用亚磷酸三乙酯进行脱硫的反应性高得多。
• Utilization of Sugars in Organic Synthesis. Part XXXIII. Thio-Sugars III. Radical Catalyzed Thione-Thiol Rearrangement of Cyclic Thionocarbonates on a Pyranose Ring: Formation of cis-Arranged Cyclic Thiolcarbonates.
  作者：Yoshisuke TSUDA、Shinsuke NOGUCHI、Kimihiro KANEMITSU、Yoshiyuki SATO、Kyoko KAKIMOTO、Yumiko IWAKURA、Shinzo HOSOI

  DOI：10.1248/cpb.45.971

  日期：——

  Pyranoside 3, 4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3, 4-thiolcarbonates of cis-stereochemistry, in accepTable yields.2, 3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides(peracetate forms) by conventional means.

  吡喃糖苷 3, 4-顺式硫代碳酸酯在自由基促进的反应条件下（方法 A、B 或 C，如本文所述）以可接受的产率生成 O-S 重排产物，即顺式立体化学的 3, 4-硫醇碳酸酯。2在方法B（用六丁基二锡烷光解）中，反式立体化学的3-硫代碳酸酯也优先产生顺式立体化学的重排产物。尽管在大多数情况下产物的区域控制并不令人满意，但一些结果表明反应的区域选择性明显受到底物异头位置的立体化学的影响。通过常规方法将产物转化为硫代糖苷（全乙酸盐形式）。
• VARELA, OSCAR;CICERO, DANIEL;DE, LEDERKREMER ROSA M., J. ORG. CHEM., 54,(1989) N, C. 1884-1890
  作者：VARELA, OSCAR、CICERO, DANIEL、DE, LEDERKREMER ROSA M.

  DOI：——

  日期：——
• A convenient synthesis of 4-thio-D-galactofuranose
  作者：Oscar Varela、Daniel Cicero、Rosa M. De Lederkremer

  DOI：10.1021/jo00269a025

  日期：1989.4