2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose | 1042397-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-sulfanyloxan-2-yl]methanol
• CAS: 1042397-88-5
• 化学式: C₂₇H₃₀O₅S
• 分子量: 466.598
• InChiKey: RHVPTWQEHMFOGB-LXSUACKSSA-N

物化性质

• 沸点：
  610.3±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose 在 四丁基硫酸氢铵 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 N-((R)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)thio)ethyl)-12-phenyldodecanamide
  参考文献：
  名称：

  双α-S-半乳糖基苯基封端神经酰胺的合成及免疫刺激活性

  摘要：

  两种携带 ω-苯基脂肪酸链的 α-S 连接的半乳​​糖神经酰胺被有效合成，并被证明对人类自然杀伤 T 细胞具有体外刺激活性。

  DOI：

  10.3998/ark.5550190.0014.224
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside 在 双(三甲基硫化硅) 、 三氟甲磺酸三甲基硅酯 、 iron perchlorate hexahydrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y

文献信息

• The First Synthesis of a Thioglycoside Analogue of the Immunostimulant KRN7000
  作者：Ravindra T. Dere、Xiangming Zhu

  DOI：10.1021/ol8019555

  日期：2008.10.16

  The first total synthesis of a thioglycoside analogue of KRN7000, a potential immunostimulant, is described. Two key intermediates are alpha-galactosyl thiol 4 and phytosphingosine derivative 5, which were both prepared from D-galactose.

  描述了KRN7000的硫代糖苷类似物（一种潜在的免疫刺激剂）的第一个全合成。两种关键中间体是α-半乳糖基硫醇4和植物鞘氨醇衍生物5，均由D-半乳糖制备。
• Alpha-GLYCOSYL THIOLS AND alpha-S-LINKED GLYCOLIPIDS
  申请人：Zhu Xiangming

  公开号：US20100184711A1

  公开（公告）日：2010-07-22

  The present invention relates to stereoselective methods for the preparation of α-glycosyl thiols and α-S-linked glycosylceramides.

  本发明涉及用于制备α-糖基硫醇和α-S-链接糖基酰胺的立体选择性方法。
• Synthesis of glycosyl disulfides containing an α-glycosidic linkage
  作者：Raymond Smith、Xiaojun Zeng、Helge Müller-Bunz、Xiangming Zhu

  DOI：10.1016/j.tetlet.2013.07.093

  日期：2013.9

  symmetrical and unsymmetrical glycosyl disulfides is synthesized with focus on the use of α-glycosyl thiols. Oxidation of α-glycosyl thiols with iodine leads to symmetrical α,α-glycosyl disulfides, while unsymmetrical disulfides are readily synthesized from α- and β-glycosyl thiols under the action of DDQ. Thus, glycosyl disulfides containing at least one α-glycosidic linkage are made available.

  合成了大量对称和不对称的糖基二硫化物，重点是α-糖基硫醇的使用。α-糖基硫醇与碘的氧化会导致对称的α，α-糖基二硫键，而不对称的二硫键很容易在DDQ作用下由α-和β-糖基硫醇合成。因此，可获得包含至少一个α-糖苷键的糖基二硫化物。
• A direct and stereospecific approach to the synthesis of α-glycosyl thiols
  作者：Ravindra T. Dere、Yingxi Wang、Xiangming Zhu

  DOI：10.1039/b804536d

  日期：——

  A new simple method for the synthesis of α-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded α-glycosyl thiols in very high yields and in a stereospecific way.

  本文介绍了一种合成δ-糖基硫醇的新的简单方法。在催化剂 TMSOTf 的作用下，1,6-酸酐糖与市售的双(三甲基硅)硫化物开环，以非常高的产率和立体特异性的方式顺利得到了δ-糖基硫醇。
• Synthesis of α-S-galactosylceramides with a truncated sphingoid chain
  作者：Xiangming Zhu、Ravindra T. Dere、Junyan Jiang

  DOI：10.1016/j.tetlet.2011.07.103

  日期：2011.9

  We present here a convenient synthesis of the truncated sphingoid iodide 15 from D-galactose, in which Mitsunobu reaction was utilized to retrieve successfully an unwanted intermediate, thereby increasing greatly the synthetic efficiency. Subsequent reaction of 15 with the pre-prepared alpha-galactosyl thiol 16 led smoothly to the desired thioglycoside 17 in good yield, from which the catabolically stable thioglycoside analogs of OCH 4 and 22 were synthesized. (C) 2011 Elsevier Ltd. All rights reserved.