phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside | 785806-29-3

• 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-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: thiophenyl 2,3,4,6-O-tetra-benzyl-α/β-D-galactopyranoside；Phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-D-galactopyranoside；(2R,3S,4S,5R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyloxane
• CAS: 785806-29-3
• 化学式: C₄₀H₄₀O₅S
• 分子量: 632.821
• InChiKey: IKCMSYGNAFDJNX-KYLXCVIJSA-N

物化性质

• 沸点：
  738.5±60.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(phenylsulfonyl)-3,4,6-tri-O-benzyl-D-galactal
  参考文献：
  名称：

  镍催化 Suzuki-Miyaura 交叉偶联 α-氧代-乙烯基砜制备 C-芳基乙二醇和无环乙烯基醚

  摘要：

  我们证明，在 Ni 催化的 Suzuki-Miyaura 交叉偶联反应中，容易获得且工作台稳定的 α-氧代乙烯基砜是有能力的亲电试剂。在这些反应中，α-氧代-乙烯基砜基序中的 C-砜键被化学选择性地裂解，以高产率提供 C-芳基乙二醇或无环乙烯基醚。这些反应在温和的条件下进行，并且可以耐受范围广泛的杂环和官能团。初步的机理研究揭示了 α-杂原子在促进这些转变中的重要性。

  DOI：

  10.1021/jacs.9b02312
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

  摘要：

  使用Zn粉和催化量的TMSCl作为活化剂，在Barbier反应条件下实现了糖1,5和1,4内酯的anomeric双二烯基化、单-β-罗汀基化和单-β-丙炔基化。合成的双二烯基衍生物经过环闭合烯烃复分解反应得到C-螺环戊烯糖苷。最后，将环戊烯环转化为基于碳水化合物的三环吗啉并三唑糖缀合物，作为潜在的SGLT2抑制剂。

  DOI：

  10.1039/c3ra46796a

文献信息

• Rapid oligosaccharide synthesis on a fluorous support
  作者：Kohtaro Goto、Tsuyoshi Miura、Daisuke Hosaka、Hiroharu Matsumoto、Mamoru Mizuno、Hide-ki Ishida、Toshiyuki Inazu

  DOI：10.1016/j.tet.2004.07.027

  日期：2004.9

  The novel fluorous support Hfb (hexakisfluorous chain-type butanoyl) was easily prepared. The Hfb group was readily introduced into the anomeric hydroxyl group of a carbohydrate, and was recyclable after cleavage. The use of the Hfb group was applicable for the rapid oligosaccharide synthesis in which the synthetic intermediates could be purified using fluorous and normal organic solvents. Each synthetic

  新型氟载体Hfb（六氟链型丁酰基）易于制备。的HFB组容易引入到异头羟基的碳水化合物的，并且是切割后可回收再利用。Hfb基团的使用适用于快速寡糖合成，其中合成中间体可以使用氟和普通有机溶剂进行纯化。每种合成中间体都可以通过TLC，NMR和质谱监测。
• Synthesis of Galactosylated Glycosylphosphatidylinositol Derivatives from<i>Trypanosoma brucei</i>
  作者：Maurice Grube、Bo-Young Lee、Monika Garg、Dana Michel、Ivan Vilotijević、Ankita Malik、Peter H. Seeberger、Daniel Varón Silva

  DOI：10.1002/chem.201705511

  日期：2018.3.2

  Trypanosoma brucei uses variant surface glycoproteins (VSGs) to evade the host immune system and ensure parasitic longevity in animals and humans. VSGs are attached to the cell membrane by complex glycosylphosphatidylinositol anchors (GPI). Distinguishing structural feature of VSG GPIs are multiple α‐ and β‐galactosides attached to the conserved GPI core structure. T. brucei GPIs have been associated

  布氏锥虫使用变体表面糖蛋白（VSG）逃避宿主免疫系统，并确保动物和人类的寄生寿命。VSG通过复杂的糖基磷脂酰肌醇锚（GPI）连接到细胞膜。VSG GPI的显着结构特征是附着在保守GPI核心结构上的多个α-和β-半乳糖苷。布氏锥虫GPIs与巨噬细胞活化和感染期间寄生虫血症的缓解有关，可作为疾病发作的延迟抗原。文献报道将GPI中的结构修饰与生物活性的变化联系起来是矛盾的。我们已经建立了一条合成路线，以制备带有不同布鲁氏梭菌的结构重叠的GPI衍生物特征性的结构修改。GPI收集物将用于评估半乳糖基化和磷酸化对布鲁氏杆菌GPI免疫调节活性的影响，并对该复杂糖脂进行表位作图，作为锥虫病的潜在诊断标记。提出了使用2-萘甲基甲基保护基合成完整的α-四氢半乳糖苷以及随后将GPI片段连接至肽的策略。
• Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides
  作者：Tsuneo Sato、Yukihiro Fujita、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/0040-4039(92)88060-i

  日期：1992.1

  Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.

  在催化量的Bu 2 Sn（OTf）2的存在下将硫代锡烷暴露于乙酰基或甲基糖苷可提供高收率的硫代糖苷。通过使用硒炔诺酮以类似的方式实现硒代糖苷化。
• Acceptor-influenced and donor-tuned base-promoted glycosylation
  作者：Stephan Boettcher、Martin Matwiejuk、Joachim Thiem

  DOI：10.3762/bjoc.8.46

  日期：——

  Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.

  碱促进的糖基化是一种最近建立的立体选择性和区域选择性方法，通过使用部分保护的受体和糖基卤代供体组装二糖和寡糖。最初的研究是在部分甲基化的受体和供体基团上进行的，作为一个模型系统，以分析氧阴离子反应性的关键原理。在这项工作中，通过使用苄基保护基团进行扩展研究，以便于制备应用。重点放在受体异构构型和供体反应性的影响上。
• Stereospecific generation and analysis of α- and β-hemiacetals of monosaccharides in gas phase
  作者：Yuki Shioiri、Katsuhiko Suzuki、Shusaku Daikoku、Ayako Kurimoto、Yukishige Ito、Osamu Kanie

  DOI：10.1016/j.carres.2013.10.001

  日期：2013.12

  A series of Boc-protected 4-aminobutyl alpha- and beta-glycosides of commonly found neutral monosaccharides were synthesized. The sodium adducted ions of these individual molecules were used in producing corresponding alpha- and beta-anomers of hemiacetal species under collision-induced dissociation (CID) conditions. The Boc group was successfully removed under CID conditions producing 4-aminobutyl glycosides, which were then used as the precursors. An intramolecular attack of the aglyconic nitrogen atom onto C-1 position of aglycon assisted to leave hemiacetal ion species without affecting anomeric configurations. In this manner, stereospecific syntheses of sugar hemiacetals were first achieved in gas phase. The dissociation of sodium cation from a series of these hemiacetals was further studied according to energy-resolved mass spectrometry. In this study, it was found that all the sugar hemiacetals could be distinguished even if they have same m/z values. Furthermore, the order of affinity of Na+ toward the hemiacetals was determined. (C) 2013 Elsevier Ltd. All rights reserved.