1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose | 63000-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose
• 英文别名: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl bromide；1-bromo-3,4,6-tri-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose；3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosylbromide；3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucosyl bromide；2-deoxy-2-phthalimido-3,4,6-tri-O-acetylglucosyl bromide；[(2R,3S,4R,5R,6R)-3,4-diacetyloxy-6-bromo-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• CAS: 63000-69-1
• 化学式: C₂₀H₂₀BrNO₉
• 分子量: 498.284
• InChiKey: GRDUQQNEXMJRRS-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose 在 吡啶 、 4-二甲氨基吡啶 、 氢气 、 palladium(II) hydroxide 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 104.0h， 生成 2-hydroxyethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

  摘要：

  Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair.

  DOI：

  10.1021/jo402700y
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-phthalimido-2-deoxy-α-D-glucopyranose 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-bromo-2-deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  碳水化合物衍生的硫醇作为质子极性反转催化剂，用于对映选择性自由基链反应

  摘要：

  已经制备并表征了多种新的同手性碳水化合物衍生的硫醇，其中SH基团连接到异头碳原子上。这些硫醇已被评估为质子极性反转催化剂，可介导三苯基硅烷向前手性亚甲基内酯中的H 2 C CR 1 R 2基团进行对映选择性自由基链加成，从而得到一般型Ph 3 SiCH 2 CHR 1 R 2的手性加合物。; 化学收率一直很高。进行了硫醇结构的系统改变，目的是增加前手性烷基Ph从SH基团夺取氢原子的对映选择性。3 SICH 2 CR 1 - [R 2。尽管在60℃下进行的反应中可以以高对映体过量获得加合物，但是与使用简单的四-O-乙酰基-β-吡喃葡萄糖和-β-甘露吡喃硫醇作为催化剂所获得的相比，对映选择性没有显着提高。据发现，吡喃糖硫醇的α端基异构体是无效的，在对映选择性介导氢的原子转移到自由基博士3 SICH 2 CR 1 - [R 2。所有的β-吡喃糖硫醇以相同的方式给出不对称诱导，但是两个具有较少极性

  DOI：

  10.1039/b202022j

文献信息

• Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides
  作者：Jiandong Liu、Chuanhu Lei、Hegui Gong

  DOI：10.1007/s11426-019-9501-4

  日期：2019.11

  This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.

  这项工作描述了通过温和的Ni催化的还原性芳基化和C 1-葡萄糖基卤化物与芳基和乙烯基卤化物的乙烯基化，立体选择性地制备β- C-芳基/乙烯基葡糖苷。广泛使用的芳基卤化物和乙烯基卤化物可产生C-芳基/乙烯基葡糖苷，产率为42％–93％。通过使用三齿配体，对C-葡糖苷获得了良好至优异的β-选择性。
• Synthesis of glycosides via indium(III) chloride mediated activation of glycosyl halide in neutral condition
  作者：Debaraj Mukherjee、Pradip Kumar Ray、Uday Sankar Chowdhury

  DOI：10.1016/s0040-4020(01)00699-8

  日期：2001.9

  Various glycosides and disaccharides were synthesized through coupling of glycosyl bromides with acceptors in presence of indium chloride as a promoter. Glycosidation reactions proceeded with high stereoselectivity.

  在氯化铟作为促进剂的存在下，通过将糖基溴化物与受体偶联，可以合成各种糖苷和二糖。糖苷化反应以高立体选择性进行。
• Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides
  作者：Zhongying Xiao、Yuxi Guo、Yunpeng Liu、Lei Li、Qing Zhang、Liuqing Wen、Xuan Wang、Shukkoor Muhammed Kondengaden、Zhigang Wu、Jun Zhou、Xuefeng Cao、Xu Li、Cheng Ma、Peng George Wang

  DOI：10.1021/acs.joc.6b00478

  日期：2016.7.15

  decades. In this study, an efficient chemoenzymatic strategy, namely core synthesis/enzymatic extension (CSEE), for rapid production of diverse HMOs was reported. On the basis of 3 versatile building blocks, 3 core structures were chemically synthesized via consistent use of oligosaccharyl thioether and oligosaccharyl bromide as glycosylation donors in a convergent fragment coupling strategy. Each of these

  人乳寡糖（HMO）是人乳中作为主要成分之一存在的各种未结合的聚糖家族。由于HMO的多样性和复杂性，其表征，定量和生物功能研究仍然是一个巨大的挑战。同类HMO库的可访问性对于解决困扰学术界数十年的这些问题至关重要。在这项研究中，报告了一种有效的化学酶策略，即核心合成/酶延伸（CSEE），用于快速生产各种HMO。在3个通用构建基的基础上，通过在收敛片段偶联策略中一致使用寡糖基硫醚和寡糖溴化物作为糖基化供体，化学合成了3个核心结构。然后，这些核心结构中的每一个都通过4种健壮的糖基转移酶扩展至多达11个HMO。化学合成31种HMO的文库，并通过MS和NMR进行表征。CSEE确实提供了一种实用的方法来为各种应用收集结构明确的HMO。
• <i>N</i>-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
  作者：Agata Walczewska、Daria Grzywacz、Dorota Bednarczyk、Małgorzata Dawgul、Andrzej Nowacki、Wojciech Kamysz、Beata Liberek、Henryk Myszka

  DOI：10.3762/bjoc.11.97

  日期：——

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.

  Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside是一种具有吸引人的药理特性的合成皂苷。我们测试了不同的途径来获得这种糖苷，这里总结了这些途径。此外，还介绍了合成葡萄糖吡喃糖苷的N-烷基和N,N-二烷基衍生物。对这些衍生物的抗菌和抗真菌活性评估表明，它们对革兰氏阴性菌没有抑制活性，而许多经过测试的N-烷基皂苷被发现抑制了革兰氏阳性菌和人类病原真菌的生长。
• Extracellular targeted drug conjugates
  申请人：Centrose, LLC

  公开号：US09364554B2

  公开（公告）日：2016-06-14

  The present invention relates to, inter alia, extracellular drug conjugates (EDC) in which an antibody or other targeting agent (e.g. a targeting moiety) is linked to a drug through a linker (e.g. a non-cleavable linker). These conjugates are useful in the treatment of disease and/or as a tool in the evaluation of biological systems.

  本发明涉及细胞外药物结合物（EDC），其中抗体或其他靶向剂（例如靶向基）通过连接剂（例如不可切割的连接剂）与药物结合。这些结合物在治疗疾病和/或作为评估生物系统工具中非常有用。