phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-((Benzoyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate；[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-phenylsulfanyloxan-2-yl]methyl benzoate
• 化学式: C₄₀H₃₂O₉S
• 分子量: 688.755
• InChiKey: LQHXMOXAHUOIQL-OJECGNTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside 在 双氧水 、 乙酸酐 、 silica gel 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以88%的产率得到phenyl 2,3,4,6-tetra-O-benzoyl-1-sulfinyl-β-D-galactopyranoside
  参考文献：
  名称：

  手性固定相简便地进行糖基亚砜的非对映分离

  摘要：

  难以分离硫手性不同的糖基亚砜的非对映异构体。本文介绍了一种使用手性固定相进行非对映体分离的快速且可扩展的方法。在20分钟内500 mg规模的分离以及三糖基亚砜非对映异构体的分离中证明了该方法的有效性。手性28：534–539，2016。©2016 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22610
• 作为产物：
  描述：

  2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 在 吡啶 、 甲醇 、 sodium methylate 作用下， 生成 phenyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Design, synthesis, and evaluation of β-galactosylceramide mimics promoting β-glucocerebrosidase activity in keratinocytes

  摘要：

  We have established an efficient synthesis of mimics of beta-galactosylceramide (beta-GalCer) increasing a beta-glucocerebrosidase (beta-GlcCer'ase) activity that associates with the skin barrier function. Among the synthetic beta-GalCer analogues (6a-6e) described herein, compound 6e exhibited a potent effect on the activation of beta-GlcCer'ase function in vitro and reduced the transepidermal water loss (TEWL) level in a UVB-induced barrier disrupted mice model. These findings indicated that compound 6e could be useful for cosmetics and medicines to improve skin barrier function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00006-4

文献信息

• Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from <i>Ascaris suum</i>
  作者：Noriyasu Hada、Yuna Umeda、Hiromi Kumada、Yoshinori Shimazaki、Kimiaki Yamano、Frank Schweizer、Naohiro Oshima、Tadahiro Takeda、Fumiyuki Kiuchi

  DOI：10.1248/cpb.c18-00768

  日期：2019.2.1

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R = biotinylated probe) were synthesized

  已经完成了立体控制的生物素标记的寡糖部分的合成，该寡糖部分包含来自glyco虫的糖鞘脂的非还原性末端寡糖。Galα1→3GalNAcβ1→OR（1），Galβ1→3Galα1→3GalNAcβ1→OR（2），Galβ1→6Galα1→3GalNAcβ1→OR（3），Galβ1→6（Galβ1→3）Galα1→3GalNAcβ1→OR（4）和Glc通过逐步缩合（1-4）和嵌段合成（5），使用5-（甲氧基羰基戊基）2-O-苯甲酰基-合成6Galβ1→6（Galβ1→3）Galα1→3GalNAcβ1→OR（5）（R =生物素化探针）。 3-O-2-萘甲基-4,6-O-二叔丁基亚甲硅烷基-α-D-吡喃半乳糖基-（1→3）-4,6-O-亚苄基-2-脱氧-2-邻苯二甲酰亚胺-β- D-吡喃半乳糖苷（12）作为常见的前体。将化合物12转化成两种糖基受体，并分别与合适的半乳糖基供体缩合。
• Improved Synthesis of 1‐Benzenesulfinyl Piperidine and Analogs for the Activation of Thioglycosides in Conjunction with Trifluoromethanesulfonic Anhydride*
  作者：David Crich、Abhisek Banerjee、Wenju Li、Qingjia Yao

  DOI：10.1081/car-200066978

  日期：2005.8.1

  piperidine in the trifluoromethanesulfonic anhydride‐mediated activation of thioglycosides, and that their less crystalline nature enables them to be used at −78°C as opposed to the −60°C required to keep 1‐benzenesulfinyl piperidine in solution. N,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric

  描述了一种大规模生产1-苯磺酰基哌啶和其他亚磺酰胺的改进方案。结果表明，在三氟甲磺酸酐介导的硫糖苷活化中，1-苯亚磺酰基吡咯烷和N，N-二乙基苯亚磺酰胺的作用类似于1-苯亚磺酰基哌啶，而且它们的结晶性较弱，因此它们可在-78°C下使用到将1-苯亚磺酰基哌啶保持在溶液中所需的-60°C。N，N-二环己基苯磺酰胺不会与三氟甲磺酸酐结合活化硫糖苷，这归因于其较大的空间体积。*致谢Jacques H. Van Boom教授。
• 1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride:  A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic Linkages
  作者：David Crich、Mark Smith

  DOI：10.1021/ja0111481

  日期：2001.9.1

  piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf(2)O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matter of minutes at -60 degrees C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with

  1-苯亚磺酰基哌啶 (BSP) 和三氟甲磺酸酐 (Tf(2)O) 的组合形成了一种新的、强大的、无金属的亲硫试剂，可以在几分钟内通过糖基三氟甲磺酸酯轻松激活武装和解除武装的硫糖苷。 -60 摄氏度，在二氯甲烷中，存在 2,4,6-三叔丁基嘧啶 (TTBP)。用醇处理后，糖基三氟甲磺酸酯以良好的收率和选择性快速而干净地转化为糖苷。
• Synthetic Studies on Glycosphingolipids from Protostomia Phyla. Synthesis of a Glycosphingolipid Analogue from the Parasite Spirometra erinacei.
  作者：Noriyasu HADA、Mayuko KURODA、Tadahiro TAKEDA

  DOI：10.1248/cpb.48.1160

  日期：——

  Novel neutral glycosphingolipids isolated from the plerocercoids of a tapeworm, Spirometra erinacei, may be expected to be involved in host-parasite interactions. We have synthesized this glycosphingolipid analogue containing 2-branched fatty alkyl residue in place of ceramide. Glycosylation of nonreducing-end trisaccharide derivative 15 with the reducing-end disaccharide derivative 17 in the presence of trimethylsilyl triflate (TMSOTf) gave the desired oligosaccharide derivative in good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycoside 19 was converted to glycosylimidate 20, which was condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated to give the target glycosphingolipid analogue 22.

  从寄生虫绦虫斯氏多头绦虫（Spirometra erinacei）的裂头蚴中分离得到的新的中性鞘糖脂可能参与宿主-寄生虫相互作用。我们合成了这种含有2-支链脂肪酸残基代替神经酰胺的鞘糖脂类似物。在三甲基硅基三氟甲磺酸酯（TMSOTf）的存在下，非还原端三糖衍生物15与还原端二糖衍生物17进行糖基化反应，得到了高产率的目标寡糖衍生物。全O-酰化的2-(三甲基硅基)乙基糖苷19被转化为糖基亚胺20，后者与2-(十四烷基)十六烷醇缩合，随后脱酰化得到目标鞘糖脂类似物22。
• Regioselective glycosylation of fully unprotected methyl hexopyranosides by means of transient masking of hydroxy groups with arylboronic acids
  作者：Eisuke Kaji、Takashi Nishino、Koji Ishige、Yohei Ohya、Yuko Shirai

  DOI：10.1016/j.tetlet.2010.01.048

  日期：2010.3

  Facile, one-pot synthesis was developed for several β(1→2)-, β(1→3)- or β(1→4)-linked disaccharides from fully unprotected methyl hexopyranosides according to the molecular recognition by arylboronic acids. The methodology was successfully applied to facile, short step assembly of the trisaccharide fragment of type II arabinogalactan.

  根据芳基硼酸的分子识别，从完全未保护的甲基己基吡喃糖苷开发了几种简单的一锅合成方法，用于几种β（1→2）-，β（1→3）-或β（1→4）连接的二糖。该方法已成功应用于II型阿拉伯半乳聚糖三糖片段的简便，短步组装。