1-thio-α,α-trehalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-thio-α,α-trehalose
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyloxane-3,4,5-triol
• 化学式: C₁₂H₂₂O₁₀S
• 分子量: 358.367
• InChiKey: SYKYBMOFPMXDRQ-LIZSDCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  206
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-thio-α,α-trehalose 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 6,6′-di-O-oleoyl-2,3,4,2′,3′,4′-hexa-O-trimethylsilyl-1-thio-α,α-D-trehalose
  参考文献：
  名称：

  Synthesis of Thioglycoside Analogues of Maradolipid

  摘要：

  We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging alpha,alpha-(1 -> 1') thioglycosidic linkage was constructed by Schmidt's inverse procedure in very high yield and excellent stereoselectivity. Subsequent protecting group manipulation and coupling with different fatty acids led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids which would be of high value for biological studies.

  DOI：

  10.1021/jo400274s
• 作为产物：
  描述：

  1,6-酸酐-2,3,4-三-O-苄基-β-D-吡喃葡萄糖 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 54.0h， 生成 1-thio-α,α-trehalose
  参考文献：
  名称：

  1-硫代海藻糖的快速合成

  摘要：

  摘要 报道了1-硫代海藻糖的两步合成。在关键的TMSOTf介导的双硫代糖基化步骤中，三-O-苄基1,6-脱水-D-葡萄糖反应物既充当糖基供体又充当糖基受体前体。在这种高度收敛的过程中，在具有高度立体控制水平的异头位置上产生了两个碳-硫键。 报道了1-硫代海藻糖的两步合成。在关键的TMSOTf介导的双硫代糖基化步骤中，三-O-苄基1,6-脱水-D-葡萄糖反应物既充当糖基供体又充当糖基受体前体。在这种高度收敛的过程中，在具有高度立体控制水平的异头位置上产生了两个碳-硫键。

  DOI：

  10.1055/s-0036-1591595

文献信息

• A facile and highly stereoselective synthesis of 1-thiotrehalose
  作者：Guohong Xin、Xiangming Zhu

  DOI：10.1016/j.tetlet.2012.05.159

  日期：2012.8

  A facile and highly stereoselective synthesis of 1-thiotrehalose, that is, α,α-S-linked trehalose, is described. Glycosylation of configurationally pure α-glucosyl thiol 5 with glucosyl trichloroacetimidate 6 or glucosyl thioimidate 9 followed by deprotection afforded 1-thiotrehalose in excellent α-stereoselectivity and high yield. A different synthetic route to the key building block, α-glucosyl thiol

  描述了一种简单且高度立体选择性的1-硫代海藻糖，即α，α- S-连接的海藻糖的合成。将构型纯的α-葡糖基硫醇5与葡糖基三氯乙酰亚氨酸酯6或葡糖基硫代亚氨酸酯9进行糖基化，然后脱保护，以优异的α-立体选择性和高收率得到1-硫代海藻糖。在此报告中，还研究了通往关键构件α-葡萄糖基硫醇5的另一种合成途径。
• Hydrogen fluoride-mediated synthesis of 1-thiotrehaloses involving reaction of d-glucose with hydrogen sulfide
  作者：Jacques Defaye、Andrée Gadelle、Christian Pedersen

  DOI：10.1016/0008-6215(91)84116-v

  日期：1991.9

  Hydrogen sulfide reacted with D-glucose in hydrogen fluoride solution to yield preponderantly alpha,alpha-1-thiotrehalose, beta,beta-1-thiotrehalose, and the alpha,beta anomer. Conditions were found under which the thiotrehaloses were obtained in the respective proportions of 8:5:5.

  硫化氢与D-葡萄糖在氟化氢溶液中反应，主要生成α，α-1-硫代海藻糖，β，β-1-硫代海藻糖和α，β异头物。发现以8：5：5的相应比例获得硫代海藻糖的条件。
• Synthesis of Thioglycoside Analogues of Maradolipid
  作者：Xiaojun Zeng、Raymond Smith、Xiangming Zhu

  DOI：10.1021/jo400274s

  日期：2013.4.19

  We describe here the first synthesis of thioglycoside analogues of maradolipid, based on a new procedure for the synthesis of 1-thiotrehalose developed recently in our laboratories. The challenging alpha,alpha-(1 -> 1') thioglycosidic linkage was constructed by Schmidt's inverse procedure in very high yield and excellent stereoselectivity. Subsequent protecting group manipulation and coupling with different fatty acids led smoothly to a group of symmetrical and unsymmetrical thiomaradolipids which would be of high value for biological studies.
• An Expeditious Synthesis of 1-Thiotrehalose
  作者：Philippe Compain、Damien Tardieu、Maria Céspedes Dávila、Damien Hazelard

  DOI：10.1055/s-0036-1591595

  日期：2018.10

  Abstract A two-step synthesis of 1-thiotrehalose is reported. In the key TMSOTf-mediated double thioglycosylation step, the tri-O-benzyl 1,6-anhydro-D-glucose reactant behaves both as a glycosyl donor and a glycosyl acceptor precursor. In this highly convergent process, two carbon-sulfur bonds are created at the anomeric positions with a high level of stereocontrol. A two-step synthesis of 1-thiotrehalose

  摘要 报道了1-硫代海藻糖的两步合成。在关键的TMSOTf介导的双硫代糖基化步骤中，三-O-苄基1,6-脱水-D-葡萄糖反应物既充当糖基供体又充当糖基受体前体。在这种高度收敛的过程中，在具有高度立体控制水平的异头位置上产生了两个碳-硫键。 报道了1-硫代海藻糖的两步合成。在关键的TMSOTf介导的双硫代糖基化步骤中，三-O-苄基1,6-脱水-D-葡萄糖反应物既充当糖基供体又充当糖基受体前体。在这种高度收敛的过程中，在具有高度立体控制水平的异头位置上产生了两个碳-硫键。