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苯基4,6-O-(苯基亚甲基)-1-硫代-BETA-D-吡喃半乳糖苷 | 138922-03-9

中文名称
苯基4,6-O-(苯基亚甲基)-1-硫代-BETA-D-吡喃半乳糖苷
中文别名
苯基 4,6-O-(苯基亚甲基)-1-硫代-BETA-D-吡喃半乳糖苷
英文名称
phenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside
英文别名
(4aR,6S,7R,8R,8aR)-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
苯基4,6-O-(苯基亚甲基)-1-硫代-BETA-D-吡喃半乳糖苷化学式
CAS
138922-03-9
化学式
C19H20O5S
mdl
——
分子量
360.431
InChiKey
BDNIQCYVYFGHSI-AQTIYHOBSA-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:
    581.2±50.0 °C(Predicted)
  • 密度:
    1.39±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    25
  • 可旋转键数:
    3
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.37
  • 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
    苯基-1-硫醇-beta-D-半乳糖苷 1-thiophenyl-β-D-galactopyranoside 16758-34-2 C12H16O5S 272.322
    2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 24404-53-3 C20H24O9S 440.471
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 74801-29-9 C40H40O5S 632.821
    —— phenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 138857-52-0 C33H28O7S 568.647
    —— 3,4-O-isopropylidene-6-O-(1-methoxy-1-methylethyl)-1-thio-β-D-galactopyranoside 270075-72-4 C19H28O6S 384.494
    —— phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 138857-53-1 C26H24O7S 480.538
    苯基-1-硫醇-beta-D-半乳糖苷 1-thiophenyl-β-D-galactopyranoside 16758-34-2 C12H16O5S 272.322
    —— phenyl 2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-1-thio-β-D-galactopyranoside 138857-83-7 C30H28O9S 564.613
    2,3,4,6-O-四乙酰基-1-硫代-β-D-苯基半乳糖苷 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 24404-53-3 C20H24O9S 440.471
    —— phenyl 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl-(1->4)-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 175978-02-6 C61H53NO14S 1056.16

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:
    参考文献:
    名称:
    具有TLR-4激动剂活性的低分子量糖的合成和免疫学评价
    摘要:
    由于缺乏FDA批准的佐剂,因此有必要合成,表征新化合物并将其用作疫苗佐剂。为此,已经从葡糖胺,丙酮酸半乳糖和1,4-环己二醇合成了一种新型的糖类似物,并在先天免疫细胞中确定了其生物学功效。更具体地说,我们评估了暴露于糖类似物后,鼠单核细胞系Raw 264.7和C57 BL / 6小鼠腹膜巨噬细胞促炎细胞因子的产生。我们的数据得出结论,如培养上清液中IL-6和TNF-α的水平升高所表明,这种新型糖类对小鼠巨噬细胞具有免疫刺激活性。该效应是TLR-4依赖性的,但与TLR-2无关的。我们的数据表明TLR-4激动;疫苗佐剂的关键特征。
    DOI:
    10.1016/j.bmc.2016.11.044
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文献信息

  • Convergent Synthesis of Sialyl Lewis<sup>X</sup>-<i>O</i>-Core-1 Threonine
    作者:Mohammed Y. R. Sardar、Appi Reddy Mandhapati、Simon Park、Walter J. Wever、Richard D. Cummings、Elliot L. Chaikof
    DOI:10.1021/acs.joc.7b03117
    日期:2018.5.4
    initial steps of inflammation. The N-terminal domain of P-selectin glycoprotein ligand-1 (PSGL-1) binds to all selectins, but with the highest affinity to P-selectin. Recent evidence suggests that the blockade of P-selectin/PSGL-1 interactions provides a viable therapeutic option for the treatment of many inflammatory diseases. Herein, we report the total synthesis of threonine bearing sialyl LewisX (sLeX)
    选择素是一类细胞粘附分子,在炎症的初始阶段起着至关重要的作用。P-选择蛋白糖蛋白配体-1(PSGL-1)的N末端结构域与所有选择蛋白结合,但对P-选择蛋白的亲和力最高。最近的证据表明,P-选择蛋白/ PSGL-1相互作用的阻断为许多炎症性疾病的治疗提供了可行的治疗选择。在此,我们报道了苏氨酸与唾液酸路易斯X(sLe X)的总合成,其连接到Core-1- O-六糖1上,作为PSGL-1 N末端结构域的关键聚糖。使用α-选择性唾液酸化和区域选择性[4 + 2]糖基化的会聚合成是该合成的关键特征。
  • From glycoside hydrolases to thioglycoligases: the synthesis of thioglycosides
    作者:Robert V. Stick、Keith A. Stubbs
    DOI:10.1016/j.tetasy.2004.12.004
    日期:2005.1
    any thioglycosides––only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.
    用适当的糖基供体和糖苷水解酶或糖合酶处理各种含活性硫醇基的糖基受体,都不能产生任何硫糖苷,只能形成O-糖基化产物。然而,当使用硫代糖基寡糖酶来介导受体和供体之间的反应时,形成了硫代糖苷。实际上,在C3,C4或C6具有巯基的吡喃糖受体(但没有C2)均能够转化为硫糖苷。给出了有关各种过程机制的一些评论。
  • Regiospecific Syntheses of <i>N</i>-Acetyllactosamine Derivatives and Application Toward a Highly Practical Synthesis of Lewis X Trisaccharide
    作者:Zhonghong Gan、Suoding Cao、Qingquan Wu、René Roy
    DOI:10.1080/07328309908544034
    日期:1999.1.1
    regiospecific glycosylation was developed by using 6-O-tert-butyldiphenylsilyl N-acetylglucosamine derivatives 3 and 5 which bear two free hydroxyl groups as acceptors. The regiospecificity was attributed to the presence of the tert-butyldiphenylsilyl group at the O-6 position of the N-acetylglucosamine derivatives. Glycosylation of suitably protected galactoside donors 10-14 with acceptors 3 and 5 gave only
    通过使用带有两个游离羟基的6 -O-叔丁基-二苯基甲硅烷基N-乙酰基葡糖胺衍生物3和5,开发了一种用于区域特异性糖基化的有效方法。区域特异性归因于在N-乙酰基葡糖胺衍生物的O -6位上存在叔丁基二苯基甲硅烷基。适当保护的半乳糖苷供体10-14与受体3和5的糖基化以良好的产率仅产生β(1→4)连接的二糖15-19。二糖18的岩藻糖基化导致路易斯X(Le x)三糖21的高产。
  • Copper(II) Triflate: A Versatile Catalyst for the One-Pot Preparation of Orthogonally Protected Glycosides
    作者:Anh-Tuan Tran、Rachel A. Jones、Julien Pastor、Julien Boisson、Nichola Smith、M. Carmen Galan
    DOI:10.1002/adsc.201100228
    日期:2011.10
    development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions
    制备正交保护的糖苷结构单元的通用方法和便捷方法对于有效合成复杂寡糖至关重要。在这里,我们描述了一种新的方法,该方法使用三氟甲磺酸铜(II)作为通用催化剂,从相应的未保护对应物一锅制备正交保护的硫代和O型糖苷。条件温和,易于处理,适用于两个和三个一锅串联转化,包括亚芳基乙缩醛化,酯化,区域选择性还原性乙缩醛开环,糖基化和甲硅烷基化过程。
  • Iodine-catalyzed one-pot acetalation–esterification reaction for the preparation of orthogonally protected glycosides
    作者:Rachel A. Jones、Robert Davidson、Anh Tuan Tran、Nichola Smith、M. Carmen Galan
    DOI:10.1016/j.carres.2010.07.010
    日期:2010.9
    An iodine-catalyzed one-pot tandem acetalation-esterification reaction of thio- and O-glycosides has been developed providing a fast and mild route to orthogonally protected glycosides ready to be used as building blocks in glycosylation reactions.
    已开发出碘催化的硫代糖苷和O-糖苷的单锅串联乙缩醛化-酯化反应,为正交保护的糖苷提供了快速温和的途径,准备将其用作糖基化反应的基础。
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