ethyl 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside | 220281-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
• 英文别名: ethyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside；(3aS,4R,6S,7R,7aR)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-ethylsulfanyl-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 220281-16-3
• 化学式: C₂₇H₃₈O₅SSi
• 分子量: 502.747
• InChiKey: GLIHBQYNNXKQLM-RXFVIIJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 溶剂黄146 作用下， 反应 5.0h， 生成 ethyl 2-O-acetyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  以 2-(三甲基甲硅烷基)乙基糖苷形式合成与痢疾志贺菌 9 型抗原重复单元相关的四糖

  摘要：

  摘要 以 D-甘露糖、D-半乳糖和 D-氨基葡萄糖盐酸盐为原料，合成了两种二糖嵌段。Schmidt 的三氯乙酰亚胺反加成技术用于构建具有 β-甘露糖苷键的双糖，收率良好。然后让两种适当形式的二糖在 N-碘代琥珀酰亚胺 (NIS) 和三氟甲磺酸 (TfOH) 存在下反应，得到四糖衍生物，从中去除保护基团得到所需的四糖形式的 2- (三甲基甲硅烷基)乙基糖苷。

  DOI：

  10.1081/scc-120028645
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 3.5h， 生成 ethyl 6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  A New Class of Branched Aminoglycosides:  Pseudo-Pentasaccharide Derivatives of Neomycin B

  摘要：

  The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.

  DOI：

  10.1021/ol035213i

文献信息

• Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from <i>Colwellia psychrerythraea</i> 34H
  作者：Giulia Vessella、Angela Casillo、Antonio Fabozzi、Serena Traboni、Alfonso Iadonisi、Maria Michela Corsaro、Emiliano Bedini

  DOI：10.1039/c9ob00104b

  日期：——

  unique capsular polysaccharide (CPS) with anti-freeze properties similar to those of the well-known anti-freeze (glyco)proteins. The tetrasaccharide repeating unit of the CPS – constituted of alternating amino sugars and uronic acid moieties in a glycosaminoglycan-like fashion with an amide-linked threonine (Thr) decoration – was synthesized as an O-n-propyl glycoside. The synthesis faced some challenging

  Colwellia psychrerythraea 34H是一种嗜冷革兰氏阴性细菌，能够通过产生独特的荚膜多糖（CPS）而在零下温度下存活，该荚膜多糖具有与众所周知的抗冻（glyco）蛋白相似的抗冻特性。合成了CPS的四糖重复单元，它是由交替的氨基糖和糖醛酸部分组成，呈类似糖胺聚糖的形式，带有酰胺连接的苏氨酸（Thr）装饰物，被合成为O-正丙基糖苷。合成面临一些挑战性的特征，例如建立拥挤的[→2）α- D -Gal p（1→]部分以及两个尿嘧啶单元仅用于在其中一个区域选择性插入Thr酰胺，得到的四糖的NMR数据证实了拟南芥（C. psychrerythraeaea）多糖的结构。
• Substituted tetrahydropyrane derivatives, method for producing same, their use as medicine or diagnostic agent, as well as medicine containing same
  申请人：Aventis Pharma Deutschland GmbH

  公开号：US06756489B1

  公开（公告）日：2004-06-29

  Substituted tetrahydropyran derivatives, processes for their preparation, their use as a pharmaceutical or diagnostic, and pharmaceutical comprising them. The invention relates to compounds of the formula I in which the radicals R1, R2, R3, R4, R5 and X have the meaning mentioned in the description, a process for the preparation of the compounds of the formula I on a solid phase, and their use as pharmaceuticals.

  取代的四氢吡喃衍生物，其制备方法，作为药用或诊断用途的使用，以及包含它们的药物。本发明涉及以下式I的化合物 其中基团R1、R2、R3、R4、R5和X的含义如描述中所述，一种在固相上制备上述式I化合物的方法，以及它们作为药物的用途。
• First Total Synthesis of the Bioactive Arylnaphthyl Lignan 4-<i>O</i> -Glycosides Phyllanthusmin D and 4′′-<i>O</i> -Acetylmananthoside B
  作者：Lei Liu、Yang Hu、Hui Liu、De-Yong Liu、Jian-Hui Xia、Jian-Song Sun

  DOI：10.1002/ejoc.201700556

  日期：2017.7.7

  Based on the orchestrated application of PTC and Yu glycosylations, the first total synthesis of arylnaphthalide glycosides, phyllanthusmin D and 4''-O-acetylmananthoside B, which were claimed to be ideal antitumoral lead compounds in terms of cytotoxicity, cytotoxic selectivity, and novel working mechanism, were achieved. With easily accessible compounds as starting materials, the two target molecules

  基于PTC和Yu糖基化的协调应用，首次全合成芳基萘苷、叶黄素D和4''-O-乙酰甘露糖苷B，这些化合物在细胞毒性、细胞毒性选择性和新颖性方面被认为是理想的抗肿瘤先导化合物工作机制，实现了。以易于获得的化合物为起始材料，以 9 步和 15 步的最长线性序列获得了两种目标分子，总产率分别为 29% 和 9%。通过合成研究，建立了有效且可扩展的合成叶木素的路线，并证实了芳基萘苷中的阻转异构现象。
• Chemical Synthesis of the Nonreducing Hexasaccharide Fragment of Axinelloside A Based on a Stepwise Glycosylation Approach
  作者：Su-Jia Li、Qing Fang、Ying-Wen Huang、Yi-Yang Luo、Xiao-Dong Mu、Ling Li、Xiao-Chen Yin、Jin-Song Yang

  DOI：10.1021/acs.orglett.2c02618

  日期：2022.10.7

  An expedient synthesis of the nonreducing hexasaccharide fragment of axinelloside A has been completed via a linear stepwise glycosylation approach. Challenges involved in the synthesis include the highly stereoselective construction of five consecutive 1,2-cis-glycosidic linkages and the formation of a sterically crowded 2,3-disubstituted l-fucoside subunit. Protecting group-directing glycosylation

  axinelloside A 的非还原性六糖片段的权宜合成已通过线性逐步糖基化方法完成。合成中涉及的挑战包括五个连续的 1,2-顺式糖苷键的高度立体选择性构建和空间拥挤的 2,3-二取代的l-岩藻糖苷亚基的形成。保护基团导向糖基化策略，例如苯甲酰基取代基的远程参与效应和 4,6- O-亚苄基的立体控制效应，用于合成所需的 1,2-顺式糖苷键。此外，2,3-支链l-岩藻糖苷框架是通过 3- O建立的然后是 2 - O糖基化序列，其中核心l-岩藻糖单元的 3-羟基首先被糖基化，然后是 2-羟基。合成六糖得到适当保护，因此可以用作合成其天然形式的前体。
• A New Class of Branched Aminoglycosides:  Pseudo-Pentasaccharide Derivatives of Neomycin B
  作者：Micha Fridman、Valery Belakhov、Sima Yaron、Timor Baasov

  DOI：10.1021/ol035213i

  日期：2003.10.1

  The clinically important antibiotic neomycin B was modified at position C5" by adding one extra sugar ring in the beta-configuration, and the observed pseudo-pentasaccharides were tested against various bacterial strains, including pathogenic and resistant strains. The designed antibiotics show antibacterial activity superior to that of neomycin B against pathogenic and resistant bacterial strains.