phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside | 310870-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-phenylsulfanyloxane-3,4,5-triol
• CAS: 310870-40-7
• 化学式: C₂₈H₃₄O₅SSi
• 分子量: 510.726
• InChiKey: FGJINLMKPNLMAY-IONQDRQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  JP5658167

  摘要：

  公开号：
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 咪唑 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 41.0h， 生成 phenyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Inositolphosphoglycan Mediators Structurally Related to Glycosyl Phosphatidylinositol Anchors: Synthesis, Structure and Biological Activity

  摘要：

  The preparation of the pseudopentasaccharide 1a, an inositolphosphoglycan (IPG) that contains the conserved linear structure of glycosyl phosphatidylinositol anchors (GPI anchors), was carried out by using a highly convergent 2+3-block synthesis approach which involves imidate and sulfoxide glycosylation reactions. The preferred solution conformation of this structure was determined by using NMR spectroscopy and molecular dynamics simulations prior to carrying out quantitative structure-activity relationship studies in connection with the insulin signalling process. The ability of 1a to stimulate lipogenesis in rat adipocites as well as to inhibit cAMP dependent protein kinase and to activate pyruvate dehydrogenase phosphatase was investigated. Compound 1a did not show any significant activity, which may be taken as a strong indication that the GPI anchors are not the precursors of the IPG mediators.

  DOI：

  10.1002/1521-3765(20001002)6:19<3608::aid-chem3608>3.0.co;2-q

文献信息

• Methyl 1,2-Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n-Pent-4-enyl 1,2-Orthoesters
  作者：Clara Uriel、Juan Ventura、Ana M. Gómez、J. Cristóbal López、Bert Fraser-Reid

  DOI：10.1002/ejoc.201200089

  日期：2012.6

  Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors – upon BF3·Et2O activation in CH2Cl2 – in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective

  吡喃甘露糖衍生的 1,2- 原乙酸甲酯 (R = Me) 和 -苯甲酸酯 (R = Ph) 可以作为糖基供体 - 在 CH2Cl2 中 BF3·Et2O 活化后 - 在与单糖受体的糖基化反应中以良好的收率提供二糖。在该过程中，糖基化优于酸催化重排，导致甲基吡喃甘露糖苷。甲基 1,2-原酸酯也可用于单糖二醇的区域选择性糖基化方案，其中它们显示出良好的区域选择性。
• A Concise Synthesis of a BODIPY-Labeled Tetrasaccharide Related to the Antitumor PI-88
  作者：Juan Ventura、Clara Uriel、Ana M. Gomez、Edurne Avellanal-Zaballa、Jorge Bañuelos、Inmaculada García-Moreno、Jose Cristobal Lopez

  DOI：10.3390/molecules26102909

  日期：——

  A convergent synthetic route to a tetrasaccharide related to PI-88, which allows the incorporation of a fluorescent BODIPY-label at the reducing-end, has been developed. The strategy, which features the use of 1,2-methyl orthoesters (MeOEs) as glycosyl donors, illustrates the usefulness of suitably-designed BODIPY dyes as glycosyl labels in synthetic strategies towards fluorescently-tagged oligosaccharides

  已经开发出一种与 PI-88 相关的四糖的聚合合成路线，该路线允许在还原端掺入荧光 BODIPY 标记。该策略的特点是使用 1,2-甲基原酸酯 (MeOE) 作为糖基供体，说明了适当设计的 BODIPY 染料作为糖基标记在荧光标记寡糖的合成策略中的有用性。
• Arias-Perez, Maria Selma; Lopez, Maria Soledad; Santos, Maria Jesus, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2002, # 9, p. 1549 - 1552
  作者：Arias-Perez, Maria Selma、Lopez, Maria Soledad、Santos, Maria Jesus

  DOI：——

  日期：——
• ——
  作者：Gregor Lemanski、Thomas Ziegler

  DOI：10.1002/1522-2675(20001004)83:10<2655::aid-hlca2655>3.0.co;2-u

  日期：2000.10.4

  A series of prearranged glycosides 5, 17, 23, 28, 37 and 41, having a benzyl-protected 1-thiomannosyl donor linked through its positions 2, 3, 4 and 6 via succinate and malonate tethers, respectively, to positions 2, 3, and 6 of a benzyl glucopyranoside acceptor, were prepared by condensation of the respective mannosyl succinates and malonates with suitably protected benzyl glucopyranosides. The prearranged glycosides were intramolecularly coupled under various conditions to give the corresponding, tethered (1 --> 4)-linked disaccharides The yields and anomer ratios of the products of these couplings were interpreted in terms of the thermodynamic stability of the resulting disaccharides. In the case of prearranged glycoside 17, having positions 3 of both the donor and the acceptor linked by a succinate tether, a strong dependence of the diastereoselectivity of the intramolecular glycosylation on the activation procedure was observed. All other cases did not show a significant dependence of the outcome of the anomeric configuration in intramolecular glycosylation on the activation procedure or the solvent.
• Access to n-pentenyl tetra- and pentasaccharide analogues of the antitumor drug PI-88 based on 1,2-methyl orthoester glycosyl donors
  作者：Juan Ventura、Clara Uriel、Ana M. Gómez、J. Cristobal López

  DOI：10.1016/j.carres.2022.108557

  日期：2022.6