allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside | 1055301-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside
• 英文别名: (3aS,4S,6R,7R,7aS)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4-prop-2-enoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1055301-74-0
• 化学式: C₂₈H₃₈O₆Si
• 分子量: 498.692
• InChiKey: XHDDANZKMMQIEJ-JMTTVTNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside 在 戴斯-马丁氧化剂 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  来自 d-甘露糖的 6-Amino-2,6-dideoxy-α-Kdo 的全合成。

  摘要：

  3-脱氧d -甘露-辛-2-糖酸（KDO）生物合成途径是在抗菌药物发现有希望的靶点。在此，我们报告了 6-氨基-2,6-双脱氧-α-Kdo 在 15 个步骤中从d-甘露糖作为 Kdo 加工酶的潜在抑制剂的全合成。合成序列的关键步骤包括用于双碳链同源化的 Horner-Wadsworth-Emmons 反应，然后是 6 -exo-trig Pd 催化的还原环化或串联 Staudinger/aza-Wittig 反应，同时伴随 α-亚氨基酯还原，使类似 Kdo 的六元氮杂环的α-立体选择性形成成为可能。

  DOI：

  10.1021/acs.orglett.0c01847
• 作为产物：
  描述：

  烯丙基alpha-D-吡喃甘露糖苷 在 咪唑 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 allyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  来自 d-甘露糖的 6-Amino-2,6-dideoxy-α-Kdo 的全合成。

  摘要：

  3-脱氧d -甘露-辛-2-糖酸（KDO）生物合成途径是在抗菌药物发现有希望的靶点。在此，我们报告了 6-氨基-2,6-双脱氧-α-Kdo 在 15 个步骤中从d-甘露糖作为 Kdo 加工酶的潜在抑制剂的全合成。合成序列的关键步骤包括用于双碳链同源化的 Horner-Wadsworth-Emmons 反应，然后是 6 -exo-trig Pd 催化的还原环化或串联 Staudinger/aza-Wittig 反应，同时伴随 α-亚氨基酯还原，使类似 Kdo 的六元氮杂环的α-立体选择性形成成为可能。

  DOI：

  10.1021/acs.orglett.0c01847

文献信息

• A General Method for Synthesis of GPI Anchors Illustrated by the Total Synthesis of the Low-Molecular-Weight Antigen from Toxoplasma gondii
  作者：Yu-Hsuan Tsai、Sebastian Götze、Nahid Azzouz、Heung Sik Hahm、Peter H. Seeberger、Daniel Varon Silva

  DOI：10.1002/anie.201103483

  日期：2011.10.10

  Building blocks: A new, general synthetic strategy, which allows the construction of branched glycosylphosphatidylinositols (GPIs), enables the synthesis of parasitic glycolipid 1 from Toxoplasma gondii. In addition, the structure is further confirmed by recognition of monoclonal antibodies.

  组成部分：一种新的通用合成策略，该策略可以构建支链糖基磷脂酰肌醇（GPI），从而可以从弓形虫中合成寄生糖脂1 。另外，通过识别单克隆抗体进一步证实了该结构。
• Synthesis of carbohydrate analogues of the THF-acetogenin 4-deoxyannomontacin and their cytotoxicity against human prostate cancer cell lines
  作者：Patricia Gonzalez Periche、Amanda Ramdular、Naga V.S.D.K. Bhupathiraju、Teja Kalidindi、Delissa S. Johnson、Nagavarakishore Pillarsetty、David R. Mootoo

  DOI：10.1016/j.carres.2022.108671

  日期：2022.11

  attracted interest for its potent cytotoxicity against a broad range of human tumor cell lines, and relatively simple structure. Herein is described the synthesis and cytotoxicity of C-10 epimers of 4-DAN and analogues thereof comprising carbohydrate and thiophene substitutes for the THF and butenolide moieties respectively. The key synthetic ploy was the union of THF and butenolide segments or their substitutes

  含有 acetogenin 4-deoxyannonmontacin (4-DAN) 的 THF 因其对多种人类肿瘤细胞系的有效细胞毒性和相对简单的结构而引起了人们的兴趣。本文描述了4-DAN及其类似物的C-10差向异构体的合成和细胞毒性，所述类似物包含分别取代THF和丁烯内酯部分的碳水化合物和噻吩。关键的合成策略是通过烯烃交叉复分解将THF和丁烯内酯片段或其替代物结合起来。不同的类似物对人前列腺癌细胞系 LNCaP 和 PC3 表现出低微摩尔至纳摩尔范围的细胞毒性。发现一种相对简单的甘露糖连接的噻吩类似物的活性与 4-DAN 相似。
• A Bioactive Synthetic Outer‐Core Oligosaccharide Derived from a <i>Klebsiella pneumonia</i> Lipopolysaccharide for Bacteria Recognition
  作者：Dushen Chen、Akhilesh K. Srivastava、Justyna Dubrochowska、Lin Liu、Tiehai Li、Joseph P. Hoffmann、Jay K. Kolls、Geert‐Jan Boons

  DOI：10.1002/chem.202203408

  日期：——

  A chemical synthesised outer core tetra- and pentasaccharide derived from the lipopolysaccharide of K. pneumoniae conjugated to the carrier proteins CRM197 and BSA elicited in mice antibodies that recognized isolated LPS as well as various strains of K. pneumoniae demonstrating they can induce relevant antigenic responses.

  化学合成的外核四糖和五糖源自肺炎克雷伯菌的脂多糖，与载体蛋白 CRM 197和 BSA 结合，在小鼠体内引发识别分离的 LPS 以及各种肺炎克雷伯菌菌株的抗体，证明它们可以诱导相关的抗原反应。
• Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose
  作者：Piotr Cmoch、Zbigniew Pakulski

  DOI：10.1016/j.tetasy.2008.05.032

  日期：2008.6

  Regioselective glycosylation of 2,3,4-unprotected benzyl alpha-D-mannopyranoside and allyl alpha- and -beta-D-mannopyranosides has been investigated. The configuration at the anomeric centre influences the outcome of the reaction. Possible role of hydrogen-bonding network in glycosylation of the above triols used as glycosidic acceptors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemoenzymatic Synthesis of <i>Campylobacter jejuni</i> Lipo-oligosaccharide Core Domains to Examine Guillain–Barré Syndrome Serum Antibody Specificities
  作者：Tiehai Li、Margreet A. Wolfert、Na Wei、Ruth Huizinga、Bart C. Jacobs、Geert-Jan Boons

  DOI：10.1021/jacs.0c08583

  日期：2020.11.18

  Guillain-Barré syndrome is often caused by Campylobacter jejuni infection that has induced antibodies to the lipo-oligosaccharide (LOS) that cross-react with gangliosides at peripheral nerves causing polyneuropathy. To examine fine specificities of anti-ganglioside antibodies and develop a more robust platform for diagnosis and disease monitoring, we developed a chemoenzymatic approach that provided an unprecedented panel of oligosaccharides composed of the inner-core of the LOS of C. jejuni extended by various ganglioside mimics. The compounds and corresponding ganglio-oligosaccharides were printed as a microarray to examine binding specificities of lectins, anti-ganglioside antibodies, and serum antibodies of GBS patients. Although lectins and anti-ganglioside antibodies did not differentiate the ganglio-oligosaccharides and mimics, the patient serum samples bound much more strongly to the ganglioside mimics. The data indicate that antibodies have been elicited to a foreign epitope that includes a heptosyl residue unique of bacterial LOS and that these antibodies subsequently cross-react with lower affinity to gangliosides. The microarray detected anti-GM1a antibodies with high sensitivity and will be attractive for diagnosis, disease monitoring, and immunological research.