p-tolyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside | 1053179-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
• 英文别名: (2S,3R,4S,5S,6S)-6-methyl-2-(4-methylphenyl)sulfanyl-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 1053179-23-9
• 化学式: C₂₇H₃₀O₄S
• 分子量: 450.599
• InChiKey: OTKVWJADKCXCNP-JHCHRPGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 溶剂黄146 、 lanthanum(lll) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 4.33h， 生成 p-methoxyphenyl 3,4-di-O-benzyl-2-O-chloroacetyl-α-L-rhamnopyranosyl(1→3)-2-O-benzyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside E and F isolated from Leonurus japonicus Houtt

  摘要：

  The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.08.014
• 作为产物：
  描述：

  p-tolyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside 、 溴甲苯 在 二正丁基氧化锡 、 四丁基碘化铵 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到p-tolyl 3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  简明合成与从毛巴拉莎（Maesa balansae）†分离的抗Leishmanial三萜类皂苷相关的五糖†

  摘要：

  据报道，从毛巴拉莎（Maesa balansae）分离得到的抗利什曼原虫三萜皂苷的糖苷部分（五糖）的合成简单。在相转移条件下已经完成了后期TEMPO介导的伯羟基氧化为羧酸的反应。糖基化通过硫代糖苷或糖基三氯乙酰亚胺酸酯的活化来进行，分别使用固定在二氧化硅（H 2 SO 4-二氧化硅）上的硫酸分别与N-碘代琥珀酰亚胺联合使用或单独使用。事实证明，与传统的路易斯酸助催化剂（如TfOH或TMSOTf）相比，H 2 SO 4-二氧化硅是更好的助催化剂。

  DOI：

  10.1021/jo801171f

文献信息

• Identification of the Minimal Glycotope of <i>Streptococcus pneumoniae</i> 7F Capsular Polysaccharide using Synthetic Oligosaccharides
  作者：Petra Ménová、Mauro Sella、Katrin Sellrie、Claney L. Pereira、Peter H. Seeberger

  DOI：10.1002/chem.201705379

  日期：2018.3.15

  diseases including meningitis, pneumonia and sepsis. Existing glycoconjugate vaccines based on purified capsular polysaccharides are widely used and help to prevent millions of deaths every year. Herein, the total syntheses of oligosaccharides resembling portions of the S. pneumoniae serotype 7F (ST7F) capsular polysaccharide repeating unit are reported. To define minimal glycan epitopes, glycan microarrays

  肺炎链球菌引起威胁生命的疾病，包括脑膜炎，肺炎和败血症。基于纯化荚膜多糖的现有糖缀合物疫苗被广泛使用，每年可帮助预防数百万人的死亡。在此，报道了类似于肺炎链球菌血清型7F（ST7F）荚膜多糖重复单元的部分的寡糖的总合成。为了定义最小的聚糖表位，含有合成寡糖的聚糖微阵列用于筛选人参血清，并揭示了ST7F的两个侧链在抗原识别中起关键作用。保护性最小表位的鉴定对于设计有效的半合成和全合成糖缀合物疫苗至关重要。
• Chemical synthesis of the tetrasaccharide repeating unit of the O-antigenic polysaccharide from Plesiomonas shigelloides strain AM36565
  作者：Rituparna Das、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2013.04.033

  日期：2013.7

  Chemical synthesis of the tetrasaccharide repeating unit of the O-antigenic polysaccharide from Plesiomonas shigelloides strain AM36565 is reported. Glycosylations between suitably protected monosaccharide synthons were achieved by the activation of thioglycosides in the presence of H2SO4-silica in conjunction with N-iodosuccinimide. The glycosylations accomplished were highly stereoselective and afforded

  报道了来自志贺氏假单胞菌菌株AM36565的O-抗原多糖的四糖重复单元的化学合成。通过在H 2 SO 4-二氧化硅和N-碘代琥珀酰亚胺的存在下硫代糖苷的活化来实现适当保护的单糖合成子之间的糖基化。所完成的糖基化是高度立体选择性的，并以良好或优异的产率提供了所需的产物。
• Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia anthina and its dimer
  作者：Xueyun Geng、Lizhen Wang、Guofeng Gu、Zhongwu Guo

  DOI：10.1016/j.carres.2016.03.023

  日期：2016.6

  A trisaccharide repeating unit of the O-antigen from Burkholderia anthina, alpha-L-Rha-(1-->2)-alpha-L-Rha-(1-->2)-beta-D-Gal-O(CH2)3NH2 (1), and its dimer, alpha-L-Rha-(1-->2)-alpha-L-Rha-(1-->2)-alpha-D-Gal-(1-->3)-alpha-L-Rha-(1-->2)-a lpha-L-Rha-(1-->2)-beta-D-Gal-O(CH2)3NH2 (2), were synthesized via a highly convergent and efficient assembly strategy. Sequential glycosylation of galactosyl acceptor

  炭疽伯克霍尔德氏菌O抗原的三糖重复单元，α-L-Rha-（1-> 2）-α-L-Rha-（1-> 2）-β-D-Gal-O（CH2 ）3NH2（1）及其二聚体，alpha-L-Rha-（1-> 2）-alpha-L-Rha-（1-> 2）-alpha-D-Gal-（1-> 3 ）-α-L-Rha-（1-> 2）-α-L-Rha-（1-> 2）-β-D-Gal-O（CH2）3NH2（2）高度收敛和高效的组装策略。半乳糖基受体6与鼠李糖基硫糖苷7的顺序糖基化，然后将所得的二糖受体9与鼠李糖基亚氨酸酯供体10缩合，在整体脱保护后得到标题分子1。标题六糖2以会聚[2 + 2 + 2]的方式组装，其中α-1,2-连接的二糖12最初是通过解除武装的硫代鼠李糖苷受体15与武装的硫代半乳糖苷供体14的偶联反应而获得的。
• Synthesis of the pentasaccharide repeating unit of the O-antigen from <i>Enterobacter cloacae</i> C4115 containing the rare α-<scp>d</scp>-FucNAc
  作者：Aritra Chaudhury、Balaram Mukhopadhyay

  DOI：10.1039/c9ra09807k

  日期：——

  Total synthesis of the pentasaccharide repeating unit associated with the O-antigen of Enterobacter cloacae C4115 is reported. The synthesis of the said oligosaccharide was accomplished through rational protecting group manipulations on commercially available monosaccharides followed by stereoselective glycosylations either by activation of thioglycosides or glycosyl trichloroacetimidates and was found

  报道了与阴沟肠杆菌C4115 的 O 抗原相关的五糖重复单元的全合成。所述寡糖的合成是通过对市售单糖进行合理的保护基操作，然后通过硫代糖苷或糖基三氯乙酰亚胺酯的活化进行立体选择性糖基化来完成的，并且发现是高效的。在这种情况下，对于稀有糖单元 α- D -FucNAc 的合成，甲氧基甲基 (MOM) 基团比早期报道的四氢吡喃 (THP) 保护更有优势。 MOM 保护的效果已成功测试用于稀有糖合成子的合成，该合成子可作为稀有D-岩藻糖胺残基的前体。
• 2,2-Dimethyl-4-(4-methoxy-phenoxy) butanoate and 2,2-Dimethyl-4-azido Butanoate: Two New Pivaloate-ester-like Protecting Groups
  作者：Riccardo Castelli、Herman S. Overkleeft、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1021/ol4008475

  日期：2013.5.3

  extend the available orthogonalities within the class of protecting groups removed by assisted cleavage. The mild, complementary (oxidative vs reductive) reaction conditions for the removal, together with their pivaloate-like character, were exploited, in combination with a levulinoyl-ester functioning as a third orthogonal protecting group, in the assembly of a Streptococcus mutans hexasaccharide

  开发了标题化合物以在通过辅助裂解除去的保护基类别内扩展可用的正交性。在组装变形链球菌六糖的过程中，开发了温和的，互补的（氧化与还原）反应条件及其类似新戊酸酯的特征，并结合了用作第三个正交保护基的乙酰丙酸酯。从具有β-葡萄糖基附肢的寡头羊骨干骨架中提取出来。