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phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside | 231623-55-5

中文名称
——
中文别名
——
英文名称
phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside
英文别名
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)-6-phenylsulfanyloxan-3-ol
phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside化学式
CAS
231623-55-5
化学式
C26H28O5S
mdl
——
分子量
452.571
InChiKey
RCNHWIGTXCJGFF-CAKRBILKSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    634.1±55.0 °C(Predicted)
  • 密度:
    1.28±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    4.4
  • 重原子数:
    32
  • 可旋转键数:
    9
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.31
  • 拓扑面积:
    93.4
  • 氢给体数:
    2
  • 氢受体数:
    6

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2
    • 3

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Mechanistic Studies and Methods To Prevent Aglycon Transfer of Thioglycosides
    摘要:
    Thioglycosides have been employed extensively for the synthesis of complex oligosaccharides, carbohydrate libraries, and mimetics of O-glycosides. While very useful, aglycon transfer is a problematic side reaction with thioglycosides. In this paper, a series of mechanistic studies are described. The aglycon transfer process is shown to affect both armed and disarmed thioglycosides, cause anomerization of the carbon-sulfur bond of a thioglycoside, and destroy the product of a glycosylation reaction. The results indicate that the aglycon transfer process can be a major problem for a wide range of thioglycosides. This side reaction is especially important to consider when carrying out complex reactions such as solid-phase glycosylations, one-pot or orthogonal multicomponent glycosylations, and construction of carbohydrate libraries. To prevent transfer, a number of modified aglycons were examined. The 2,6-dimethylphenyl ( DMP) aglycon was found to effectively block transfer in a variety of model studies and glycosylation reactions. The DMP group can be installed in one step from a commercially available thiol ( 2,6-dimethylthiophenol) and is useable as a glycosyl donor. On the basis of these features, the DMP group is proposed as a convenient and improved aglycon for thioglycosides.
    DOI:
    10.1021/ja063247q
  • 作为产物:
    描述:
    phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside溶剂黄146 作用下, 以 为溶剂, 反应 1.0h, 以96%的产率得到phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside
    参考文献:
    名称:
    耻垢分枝杆菌 首次完全合成含有海藻糖的四糖†
    摘要:
    首次报道了从耻垢分枝杆菌分离的三种重要的含海藻糖的四糖的全合成,其中使用亚苄基乙缩醛的区域选择性开放和立体选择性糖基化为关键步骤。糖基化反应中的1,2-顺式立体选择性是使用来自远程参与小组的邻氨基苯甲酸酯协助,空间效应和溶剂参与而实现的。合成策略也可用于组装来自结核分枝杆菌的结构相关的低聚糖。
    DOI:
    10.1039/c6ob00412a
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文献信息

  • An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)
    作者:Katsuhiko Suzuki、Yukishige Ito、Osamu Kanie
    DOI:10.1016/j.carres.2012.07.003
    日期:2012.10
    examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded without N-bromosuccinimide (NBS), in some cases it was found that the electrophilicity of the Vilsmeier-type electrophilic sulfinium cation species was not sufficient for the activation of certain less-reactive thioglycosides. Here, we report the results of fluorination reactions of a series of monosaccharides using
    使用N,N-二乙基基三DAST)检查了糖苷直接转化为寡糖合成中常用的糖基化物。尽管反应在没有N-代琥珀酰亚胺NBS)的情况下进行,但在某些情况下,发现Vilsmeier型亲电electro阳离子物种的亲电性不足以活化某些反应性较低的代糖苷。在这里,我们报告了在不存在NBS的情况下使用DAST进行的一系列单糖化反应的结果,并讨论了在存在二甲基(甲基)s三甲烷磺酸盐(DMTST)的情况下加速反应的过程,从而提高了产品收率。
  • Glycosylations Directed by the Armed-Disarmed Effect with Acceptors Containing a Single Ester Group
    作者:Thomas H. Schmidt、Robert Madsen
    DOI:10.1002/ejoc.200700347
    日期:2007.8
    A selective glycosylation reaction controlled by the armed-disarmed effect is described by the use of phenyl thioglycosides. The donor thioglycoside is fully protected with benzyl ethers while the acceptor thioglycoside contains benzyl ethers at position 2 and 3 and a strongly electron-withdrawing pentafluorobenzoate ester group at position 6. The coupling can be performed with galactose, glucose,
    通过使用苯基糖苷描述了由武装-解除武装效应控制的选择性糖基化反应。供体糖苷被苄基醚完全保护,而受体糖苷在 2 位和 3 位包含苄基醚,在 6 位包含一个强吸电子的五苯甲酸酯基团。偶联可以用半乳糖葡萄糖甘露糖和邻苯二甲酰亚胺保护葡萄糖胺以良好的产率提供相应的 1,4-连接的二糖。如果添加另一个受体和更多的促进剂,这些二糖可以作为糖基供体在同一个锅中进行额外的偶联反应。这样,可以在一次操作中实现两次连续的糖基化以提供三糖。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
  • Synthesis of the <i>Staphylococcus aureus</i> Strain M Capsular Polysaccharide Repeating Unit
    作者:Bas Hagen、J. Hessel M. van Dijk、Qingju Zhang、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée
    DOI:10.1021/acs.orglett.7b00747
    日期:2017.5.19
    The synthesis of the Staphylococcus aureus strain M capsular polysaccharide repeating unit is reported. A postglycosylation oxidation strategy was utilized for the construction of the α-galactosaminuronic acid linkages, relying on a stereoselective 2-azido-4,6-O-di-tert-butylsilylidene galactopyranoside donor, for which the selectivity was assessed by model glycosylations. The α-fucosamine linkage
    报道了黄色葡萄球菌菌株M荚膜多糖重复单元的合成。甲postglycosylation氧化策略用于α-galactosaminuronic酸键的结构,依靠立体选择性2-叠氮基-4,6- ø -二-叔-butylsilylidene喃半乳糖苷供体,的量,选择性通过模型糖基化进行评估。使用反应性2-叠氮基岩藻糖基供体选择性地安装α-岩藻糖胺键。TEMPO / PhI(OAc)2 -Pinnick氧化规避了在TEMPO / PhI(OAc)2介导的二糖中间体氧化过程中发生的意外糖苷键断裂。
  • Influence of the 4,6-<i>O</i>-Benzylidene, 4,6-<i>O</i>-Phenylboronate, and 4,6-<i>O</i>-Polystyrylboronate Protecting Groups on the Stereochemical Outcome of Thioglycoside-Based Glycosylations Mediated by 1-Benzenesulfinyl Piperidine/Triflic Anhydride and <i>N</i>-Iodosuccinimide/Trimethylsilyl Triflate
    作者:David Crich、Marco de la Mora、A. U. Vinod
    DOI:10.1021/jo0349882
    日期:2003.10.1
    The effect of 4,6-O-benzylidene acetals, 4,6-O-phenylboronate esters, and 4,6-O-polystyrylboronate esters on the stereoselectivity of couplings to galacto-, gluco-, and mannopyranosyl thioglycosides, otherwise protected with benzyl ethers, has been investigated by the benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride (BSP), diphenyl sulfoxide/trifluoromethanesulfonic anhydride (Ph(2)SO), and
    4,6-O-亚苄基乙缩醛,4,6-O-苯基硼酸酯和4,6-O-聚苯乙烯硼酸酯对与半乳糖葡萄糖和甘露喃糖基糖苷偶联的立体选择性的影响,否则用苄基保护醚,已通过苯亚磺酰基哌啶/三氟甲磺酸酐BSP),二苯亚砜/三氟甲磺酸酐(Ph(2)SO)和N-代琥珀酰亚胺/三甲基甲硅烷三氟甲磺酸盐(NIS / TMSOTf)方法进行了研究。BSP和Ph(2)SO方法在所有三个系统中均提供了可比的结果,而NIS方法在葡萄糖甘露糖中却提​​供了显着不同的立体选择性,而在半乳糖系列中却没有。亚苄基乙缩醛硼酸酯在β-选择性甘露糖系列和α-选择性半乳糖系列中以相似的方式影响立体化学,但与葡萄糖供体显示出显着差异。葡萄糖,半乳糖甘露糖系列之间的差异反映了已建立的反应性差异,尤其是对于甘露糖而言,其端基异构作用方面的差异,并且最好根据α-和β-共价三氟甲磺酸酯中间体之间相对能的变化来解释以及它们必须平衡的各种接触离子对。
  • FORMAL SYNTHESIS OF CYTOSAMINE—A COMPONENT OF NUCLEOSIDE ANTIBIOTICS, THE AMICETIN FAMILY
    作者:Hideyuki Sugimura、Ken-ichi Watanabe
    DOI:10.1081/scc-100104831
    日期:2001.1
    A facile route to a synthetic precursor of the nucleoside antibiotics, amicetins, was investigated employing stable phenyl thioglycosides as key building blocks.
    使用稳定的苯基糖苷作为关键构建块,研究了合成核苷抗生素前体阿米西汀的简便途径。
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