1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose | 104486-80-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose
• 英文别名: (6S)-6-(Acetoxymethyl)-1-O,2-O,3-O,4-O,6-O-pentakisacetyl-alpha-D-mannopyranose；[(2S)-2-acetyloxy-2-[(2R,3R,4S,5S,6R)-3,4,5,6-tetraacetyloxyoxan-2-yl]ethyl] acetate
• CAS: 104486-80-8
• 化学式: C₁₉H₂₆O₁₃
• 分子量: 462.408
• InChiKey: QZKAVUYSOOSMDY-ZOFHRBRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 生成 2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid
  参考文献：
  名称：

  Synthesis of methyl 3-O-(α-d-glucopyranosyl)-7-O-(l-glycero-α-d-manno-heptopyranosyl)-l-glycero-α-d-manno- heptopyranoside

  摘要：

  The title trisaccharide glycoside, which is related to part of the core region of the lipopolysaccharide from Salmonella, and the disaccharide glycosides methyl 3-O-alpha-D-glucopyranosyl-L-glycero-alpha-D-manno-heptopyranoside and methyl 7-O-L-glycero-alpha-D-manno-heptopyranosyl-L-glycero-alpha-D-manno- heptopyranoside have been synthesised. Methyl 2,3,4-tri-O-benzyl-L-glycero-alpha-D-manno- heptopyranoside, obtained via a one-carbon elongation at C-6 of methyl 2,3,4-tri-O-benzyl-alpha-D-manno- hexodialdo-1,5-pyranoside, was used as precursor both for the heptosyl donor and acceptor.

  DOI：

  10.1016/0008-6215(90)80133-n
• 作为产物：
  描述：

  methyl L-glycero-α-D-manno-heptopyranoside 以74%的产率得到
  参考文献：
  名称：

  BOONS, G. J. P. H.;MAREL, G. A. VAN DER;POOLMAN, J. T.;BOOM, J. H. VAN, REC. TRAV. CHIM. PAYS-BAS., 108,(1989) N0, C. 339-343

  摘要：

  DOI：

文献信息

• The Mechanism of the Reaction Catalyzed by ADP-β-<scp>l</scp>-<i>g</i><i>lycero</i>-<scp>d</scp>-<i>m</i><i>anno</i>-heptose 6-Epimerase
  作者：Jay A. Read、Raef A. Ahmed、James P. Morrison、William G. Coleman,、Martin E. Tanner

  DOI：10.1021/ja0485659

  日期：2004.7.1

  nonstereospecific oxidation/reduction directly at C-6' '. It was found that the epimerization proceeds without any detectable incorporation of solvent-derived deuterium or 18O-isotope into the product. This argues against mechanisms involving either proton transfers at carbon or dehydration/rehydration events. In addition, the deoxygenated analogues, 7' '-deoxy-ADP-l,d-Hep and 4' '-deoxy-ADP-l,d-Hep, were both found

  ADP-l-甘油-d-甘露糖-庚糖 6-差向异构酶 (AGME, RfaD) 是一种细菌酶，参与脂多糖生物合成并相互转化 ADP-β-l-甘油-d-甘露糖-庚糖 (ADP-l,d -Hep) 与 ADP-β-d-甘油-d-甘露糖-庚糖 (ADP-d,d-Hep)。已知 AGME 需要紧密结合的 NADP+ 辅因子才能发挥活性，并且可能采用一种涉及底物瞬时氧化的机制。四种机制可能性被认为涉及庚糖核苷酸的 C-7''、C-6'' 或 C-4'' 处的瞬时氧化。在这项贡献中，溶剂同位素掺入研究和替代底物的使用为直接在 C-6' ' 上涉及非立体特异性氧化/还原的机制提供了强有力的证据。发现差向异构化在没有任何可检测的溶剂衍生的氘或 18O-同位素掺入产物的情况下进行。这反对涉及碳质子转移或脱水/再水化事件的机制。此外，发现脱氧类似物 7''-脱氧-ADP-1,d-Hep 和 4''-脱氧-ADP-1
• Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-<i>O</i>-acetyl-<scp>L</scp>-<i>glycero-</i>α-<scp>D</scp>-<i>manno</i>-heptopyranose
  作者：Christian Stanetty、Ian R. Baxendale

  DOI：10.1002/ejoc.201500024

  日期：2015.4

  The higher-carbon sugar l-glycero-d-manno-heptose is a major constituent of the inner core region of the lipopolysaccharide (LPS) of many Gram-negative bacteria. All preparative routes used to date require multiple steps, and scalability has been rarely addressed. Here a highly practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-l-glycero-alpha-d-manno-heptopyranose by a simple four-step sequence

  高碳糖的l-甘油-d-甘露糖庚糖是许多革兰氏阴性细菌的脂多糖（LPS）的核心区域的主要组成部分。迄今为止，所有准备路线都需要多个步骤，而可扩展性很少得到解决。在此公开了一种高度实用的合成晶体1,2,3,4,6,7-六-O-乙酰基-1-甘油-α-d-甘露聚糖-七吡喃糖的简单方法，该方法是从l-lyxose开始的简单四步顺序进行的。仅需要两次重结晶，并且该过程以> 100 mmol的规模进行了证明，得到41 g的目标化合物。
• The Inhibition of Liposaccharide Heptosyltransferase WaaC with Multivalent Glycosylated Fullerenes: A New Mode of Glycosyltransferase Inhibition
  作者：Maxime Durka、Kevin Buffet、Julien Iehl、Michel Holler、Jean-François Nierengarten、Stéphane P. Vincent

  DOI：10.1002/chem.201102052

  日期：2012.1.9

  (L‐glycero‐D‐manno‐heptopyranoses) are found in important bacterial glycolipids such as lipopolysaccharide (LPS), the biosynthesis of which is targeted for the development of novel antibacterial agents. This work describes the synthesis of a series of fullerene hexa‐adducts bearing 12 copies of peripheral sugars displaying the mannopyranose core structure of bacterial l,d‐heptoside. The multimers were assembled

  在重要的细菌糖脂（例如脂多糖（LPS））中发现了l，d-庚糖苷（L-甘油-D-甘露聚糖-庚糖），其生物合成旨在开发新型抗菌剂。这项工作描述了一系列富勒烯六加合物的合成，这些加合物带有12个拷贝的外围糖，显示了细菌l，d-庚酮的甘露吡喃糖核心结构。最后一步是通过有效的铜催化炔烃-叠氮化物环加成反应组装多聚体。将最终的富勒烯糖球作为庚基转移酶WaaC的抑制剂进行分析，该糖基转移酶催化第一个L的掺入将庚糖转化为LPS。有趣的是，最终分子的抑制在低微摩尔范围被发现（IC 50 = 7-45μ中号），而相应的单体苷显示高微摩尔至毫摩尔低抑制水平（IC 50总是高于400μ中号）。当以“每糖”为基础进行评估时，这些抑制数据表明，在每种情况下，富勒烯的一个糖苷对WaaC的平均亲和力在以多聚体形式显示时均得到显着增强，从而证明了意想不到的多价效应。迄今为止，从未用糖基转移酶证实过这种多价抑制方式。
• Synthesis of 2-(4-trifluoroacetamidophenyl)ethyl O-(spL-glycero-α-spD-manno-heptopyranosyl)-(1→7)-O-(spL-glycero-α-spD- manno-heptopyranosyl)-(1»3)-spL-glycero-α-spD-manno-heptopyranoside, coresponding to the heptose region of the Salmonella Ra core structure
  作者：Per J. Garegg、Stefan Oscarson、Helena Ritzén、Maria Szönyi

  DOI：10.1016/s0008-6215(00)90553-6

  日期：1992.4

  Abstract The title trisaccharide was synthesized from methyl 2,3,4-tri- O -benzyl- L - glycero -α- D - manno -heptopyranoside by acetolysis, followed by conversion into ethyl thioglycosides and also glycosyl bromides, which were borth used in glycoslyation reactions. In glycosylations using thioglycosides as glycosyl donors, N -iodosuccinimide-silver triflate and dimethyl(methylthio)sulfonium triflate

  摘要标题化合物由2,3,4-三-O-苄基-L-甘油-α-D-甘露聚糖-七吡喃糖苷经乙酰水解合成，然后转化为乙基硫代糖苷和糖基溴化物。糖基化反应。在使用硫代糖苷作为糖基供体的糖基化中，将N-碘代琥珀酰亚胺-三氟甲磺酸银和三氟甲磺酸二甲基（甲硫基）as用作促进剂，并且在与糖基溴化物的糖基化中使用三氟甲磺酸银。设计在标题三糖合成过程中引入中间体的保护基团，以允许在O-3'处进行稍后的糖基化反应，以产生沙门氏菌LPS核心区域的较大寡糖片段，并允许在O-4和0-4'，
• Synthesis of linear oligosaccharides: l-glycero-α-d-manno-heptopyranosyl derivatives of allyl α-glycosides of d-glucose, kojibiose, and 3-O-α-kojibiosyl-d-glucose, substrates for synthetic antigens
  作者：Sergey A. Nepogod'ev、Leon V. Backinowski、Barbara Grzeszczyk、Aleksander Zamojski

  DOI：10.1016/0008-6215(94)84242-6

  日期：1994.2

  Synthesis of the title oligosaccharides was performed with the use of peracetylated L-glycero-beta-D-manno-heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosyl accepters bearing acyl and acetal protecting groups.