Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate | 85382-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate
• 英文别名: methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-oct-2-ulopyranosyl bromide)onate；methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)onate；methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-D-manno-oct-2-ulopyranosyl bromide)onate；Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-D-manno-2-octulopyranosyl bromide)onate；methyl (2S,4R,5R,6R)-4,5-diacetyloxy-2-bromo-6-[(1R)-1,2-diacetyloxyethyl]oxane-2-carboxylate
• CAS: 85382-87-2
• 化学式: C₁₇H₂₃BrO₁₁
• 分子量: 483.267
• InChiKey: BNXFUUJAWUOASC-DRXUAVOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate 在 1,3-丙二醇 4 A molecular sieve 、 氢气 、 silver trifluoromethanesulfonate 、 氰化汞 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 68.0h， 生成 methyl 5-O-benzoyl-3-O-(4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosylono-1',2-lactone)-β-D-ribofuranoside
  参考文献：
  名称：

  包含与d-核糖二级位置相连的3-deoxy-α-d-manno-2-octulosonicacid（KDO）的大肠杆菌LP 1092荚膜多糖的交替线性和分支重复单元

  摘要：

  寡糖，3-O-（3-脱氧-α-D-甘露糖-2-辛基吡喃果糖酸钠）-β-D-呋喃呋喃糖苷e，甲基2-O-β-D-呋喃呋喃糖基-3-O-（钠3 -脱氧-α-D-甘露糖-2-辛基吡喃磺酸钠）-β-D-呋喃呋喃糖苷e和甲基O-（3-脱氧-α-D-甘露糖-2-辛基吡喃磺酸钠）-（2 ---- 2）以高纯度和良好的整体收率制备了-O-β-D-呋喃呋喃糖基-（1 ---- 2）-β-D-呋喃呋喃糖苷。三糖衍生物的组成对应于大肠杆菌LP 1092荚膜多糖的线性和支链结构的重复单元。alpha-KDO-（2 ---- 3）-beta-D-Ribf和α-KDO-（2 ---- 2）-β-D-Ribf单元是通过修改Helferich程序并使用甲基（4,5,7，8-四-O-乙酰基-3-脱氧-α-D-甘露糖-2-辛基吡喃糖基溴化物）-酸酯和适当的β-D-核呋喃糖基衍生物。组成和构型分配基于寡糖的受保护衍生物的250-MHz

  DOI：

  10.1016/s0008-6215(00)90455-5
• 作为产物：
  描述：

  methyl 4,5,7,8-tetra-O-acetyl-3-deoxyl-alpha-D-manno-2-octulopyranosonate 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 Methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-α-D-manno-2-octulopyranosyl bromide)-onate
  参考文献：
  名称：

  Evaluation of thioglycosides of Kdo as glycosyl donors

  摘要：

  The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good beta-anomeric selectivity. The use of diethyl ether as solvent and (especially) isopropylidene acetals as protecting groups improved the alpha-anomeric selectivity. NIS/AgOTf as promoter surprisingly yielded the 3-iodo-product via the glycal intermediate. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.021

文献信息

• Synthesis of Neoglycoconjugates Containing 4-Amino-4-deoxy-L-arabinose Epitopes Corresponding to the Inner Core of Burkholderia and Proteus Lipopolysaccharides
  作者：Markus Blaukopf、Bernhard Müller、Andreas Hofinger、Paul Kosma

  DOI：10.1002/ejoc.201101171

  日期：2012.1

  spacer glycosides, which were efficiently coupled to maleimide-activated bovine serum albumin. The neoglycoconjugates serve as immunoreagents with specificity for inner core epitopes of Burkholderia and Proteus lipopolysaccharides.

  摘要 含有 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) 和 d-glycero-d-talo-oct-2-ulosonic acid (Ko) 8 位被 4-氨基取代的二糖。已制备 4-脱氧-β-1-阿拉伯吡喃糖基 (Ara4N) 残基。将 N-苯基三氟乙酰亚胺酸酯-4-叠氮基-4-脱氧-1-阿拉伯糖基糖基供体偶联到 Kdo 和 Ko 的乙酰基保护的烯丙基糖苷上，分别以 74% 和 90% 的产率提供了二糖产物的异头混合物，通过色谱法将其分离。中间体 Ara4N-(1→8)-Kdo 二糖受体的进一步延伸，利用与 Kdo 溴化物供体在 Helferich 条件下的区域选择性糖基化，提供支链三糖 α-Kdo-(2→4)[β-l- Ara4N-(1→8)]-α-Kdo 衍生物。受保护的二糖和三糖烯丙基糖苷的脱保护是通过 TiCl4 促进的苄醚裂解来完成的，
• Synthesis of pentasaccharide core structures corresponding to the genus-specific lipopolysaccharide epitope of Chlamydia
  作者：Paul Kosma、Martina Strobl、Günter Allmaier、Erich Schmid、Helmut Brade

  DOI：10.1016/0008-6215(94)84246-9

  日期：1994.2

  dium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->6)-O-2-aceta mid o-2-deoxy- beta-D-glucopyranosyl-(1-->6)-2-acetamido-2-deoxy-alpha- and -beta-D-glucopyranoside (19a and 19b), and the pentasaccharides allyl O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->4)-O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->6)-O-2-aceta

  制备6）-2-乙酰胺基-2-脱氧-α-和-β-D-吡喃葡萄糖苷（23a和23b）。糖苷键是使用1,3,4,6-四-O-乙酰基-2-氯乙酰胺基-2-脱氧-β-D-葡萄糖吡喃糖（6）和FeCl3作为促进剂以及过O-乙酰化的在Helferich条件下，Kdo单糖和二糖溴化物衍生物（12和20）。寡糖，对应于肠杆菌和衣原体脂多糖的去磷酸化的部分结构，通过NMR光谱以及血浆脱附和基质辅助激光脱附质谱进行了表征。6-四-O-乙酰基-2-氯乙酰胺基-2-脱氧-β-D-葡萄糖吡喃糖（6）和FeCl3作为促进剂，以及过O-乙酰化的Kdo单糖和二糖溴化物衍生物（12和20）在Helferich条件下。寡糖，对应于肠杆菌和衣原体脂多糖的去磷酸化的部分结构，通过NMR光谱以及血浆脱附和基质辅助激光脱附质谱进行了表征。6-四-O-乙酰基-2-氯乙酰胺基-2-脱氧-β-D-葡萄糖吡喃糖（6）和FeCl3作为促进剂，以
• Synthesis of neoglycoproteins containing d-glycero-d-talo-oct-2-ulopyranosylonic acid (Ko) ligands corresponding to core units from Burkholderia and Acinetobacter lipopolysaccharide
  作者：Norbert Wimmer、Helmut Brade、Paul Kosma

  DOI：10.1016/s0008-6215(00)00213-5

  日期：2000.11

  intermediates, which were transformed into D-glycero-D-talo-oct-2-ulopyranosylonic acid (Ko), as well as 3-O- and 4-O-p-nitrobenzoyl-Ko derivatives. The exo-allyl orthoester derivative, methyl [5,7,8-tri-O-acetyl-4-O-(4-nitrobenzoyl)-2,3-O-[(1-exo-allyloxy)-ethylidene]-D-glycero-beta-D-talo-oct-2-ulopyranos]onate, prepared from the 4-O-pNBz-protected Ko derivative, was elaborated into the alpha-Ko allyl

  将Kdo衍生物的乙二醇酯转化为2,3-脱水中间体，然后将其转化为D-甘油-D-talo-oct-2-ulyryranosylonic acid（Ko）以及3-O-和4-Op-硝基苯甲酰基-Ko衍生物。外烯丙基原酸酯衍生物，甲基[5,7,8-三-O-乙酰基-4-O-（4-硝基苯甲酰基）-2,3-O-[（1-外-烯丙氧基）-亚乙基] -D由4-O-pNBz保护的Ko衍生物制备的-甘油-β-D-talo-oct-2-ulopyranos] onate被精制为α-Ko烯丙基酮糖苷，即还原性二糖α-Kdop-（2- -> 4）-Ko和二糖α-Kdop-（2-> 4）-Kop-（2-> OAll）。相反，[4,5,7,8-四-O-乙酰基-3-O-（4-硝基苯甲酰基）-甲基-D-甘油-D-talo-2-辛基吡喃糖基溴化]甲酸甲酯[碳水化合物。Res。，244（1993）69-84]，与Kdo受体偶联，得到二糖α-Kop-（2->
• Synthesis of α-Kdo-(2→4)-Kdo disaccharide derivatives and their conjugation with a protected form of GLA-60, a biologically active analog of a lipid a subunit
  作者：Makoto Kiso、Minoru Fujita、Yuji Ogawa、Hideharu Ishida、Akira Hasegawa

  DOI：10.1016/0008-6215(90)84106-5

  日期：1990.2

  A variety of the protected O-[(3-deoxy-alpha-D-manno-2-octulopyranosyl)onic acid]-(2----4)-3-deoxy-D-manno-2-octulosonic acid [alpha-Kdo-2(2----4)-Kdo] derivatives have been synthesized starting from methyl [2-(trimethylsilyl)ethyl 4,5,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosid] onate. Some of these were conjugated with a protected form of a bacterial lipid A subunit-analog (GLA-60)

  各种受保护的O-[（3-脱氧-α-D-甘露聚糖-2-辛基吡喃糖基）磺酸]-（2 ---- 4）-3-脱氧-D-甘露糖-2-辛基磺酸[α从甲基[2-（三甲基甲硅烷基）乙基4,5,7,8-四-O-乙酰基-3-脱氧-α-D开始合成-Kdo-2（2 ---- 4）-Kdo]衍生物-manno-2-octulopyranosid] onate。其中一些与具有有益免疫药理活性的细菌脂质A亚基类似物（GLA-60）的保护形式缀合，即苄基2-[（（3R）-3-（苄氧基-甲氧基）四癸酰胺基] -2-脱氧- 4-O-（二苯氧基次膦酰基）3-O-[（（3R）-3-十四烷酰氧基十四烷酰+ ++]-β-D-吡喃葡萄糖苷。
• Synthesis of poly(acrylamide) copolymers containing 3,5-dideoxy-d-arabino-2-octulopyranosylonic acid (5-deoxy-Kdo) residues
  作者：Paul Kosma、Peter Waldstätten、Laurent Daoud、Gerhard Schulz、Frank M. Unger

  DOI：10.1016/0008-6215(89)85014-1

  日期：1989.12

  glycosylation of allyl alcohol or methyl (allyl 7,8-O-carbonyl-3,5-dideoxy-α- d -arabino-2-octulopyranosid)onate with Kdo or 5-deoxy-Kdo bromide derivatives, respectively. Removal of the protecting groups and subsequent copolymerization of the allyl glycosides with acrylamide gave artificial antigens suitable for the determination of epitope specificities displayed by monoclonal antibodies directed

  摘要单糖钠（烯丙基3,5-二脱氧-α-和-β-d-阿拉伯糖-2-辛基吡喃葡萄糖苷）和二糖O- [钠（3-脱氧-α-d-甘露糖-2-）辛基吡咯烷酮基]]]>（（2→4）-]（3,5-二烯丙基-α-d-阿拉伯糖基-2-辛基吡喃果糖基烯丙基）（相应于Kdo-单糖和-di-糖的5-脱氧衍生物），通过烯丙基醇或甲基（烯丙基7,8-O-羰基-3,5-二脱氧-α-d-阿拉伯糖基-2-八氟吡喃糖苷）与Kdo或5-脱氧-烯丙基的氰化汞（II）氰化促进的糖基化反应合成Kdo溴化物衍生物。除去保护基并随后使烯丙基糖苷与丙烯酰胺共聚，得到了适于确定由针对肠杆菌脂多糖的Kdo区的单克隆抗体所展示的表位特异性的人造抗原。