6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose | 497096-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose
• 英文别名: [(2R,3S,4R,5S,6S)-5-azido-6-hydroxy-3,4-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 497096-15-8
• 化学式: C₂₂H₂₅N₃O₆
• 分子量: 427.457
• InChiKey: GKZFEMRXZMCDPE-YHINDDMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  88.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 在 吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 三甲基乙酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 nickel dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 triethylammonium 2-(benzyloxycarbonyl)aminoethyl 2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranoside 6-(2-acetamido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranosyl phosphate)
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.

  DOI：

  10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1
• 作为产物：
  描述：

  1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose 在 二甲胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A

  摘要：

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.

  DOI：

  10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1

文献信息

• A process for the preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose
  申请人：Adamed sp. z o.o.

  公开号：EP2374809A1

  公开（公告）日：2011-10-12

  The invention relates to a process for the preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, which process comprises reaction of 1,6-anhydro-2-azido-2-deoxy-D-glucopyranose with benzyl bromide in acetonitrile in the presence of solid sodium hydroxide to form 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose; subsequent reaction of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose with acetic anhydride in the presence of trifluoroacetic acid to form 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose; and treatment of 1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose with piperidine in THF. 6-0-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose is useful as a building block for synthesis of glucosamine oligosaccharides.

  该发明涉及一种制备6-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃的方法，该方法包括将1,6-脱水-2-叠氮基-2-去氧-D-葡萄糖吡喃与苄溴在乙腈中，在固体氢氧化钠存在下反应，形成1,6-脱水-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃；随后将1,6-脱水-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃与乙酸酐在三氟乙酸存在下反应，形成1,6-二-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃；并用哌啶在THF中处理1,6-二-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃。6-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-去氧-D-葡萄糖吡喃可用作合成氨基葡萄糖寡糖的构建块。
• A process for the preparation of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose
  申请人：Adamed sp. z o.o.

  公开号：EP2374810A1

  公开（公告）日：2011-10-12

  The invention relates to a process for the preparation of 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, consisting of reaction of 1,6-anhydro-2-azido-2-deoxy-D-glucopyranose with benzyl bromide in a mixture of aromatic organic solvent and dipolar aprotic solvent and in the presence of a mixture of solid sodium hydroxide with solid potassium carbonate, phase transfer catalyst and tertiary alcohol. 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose is useful for preparation of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose, a building block for synthesis of glucosamine oligosaccharides.

  该发明涉及一种制备1,6-去水-2-叠氮基-3,4-二-O-苄基-2-脱氧-D-葡萄糖吡喃的过程，包括将1,6-去水-2-叠氮基-2-脱氧-D-葡萄糖吡喃与苄基溴在芳香性有机溶剂和双极无水溶剂的混合物中，在固体氢氧化钠与固体碳酸钾的混合物、相转移催化剂和三级醇的存在下反应。1,6-去水-2-叠氮基-3,4-二-O-苄基-2-脱氧-D-葡萄糖吡喃可用于制备6-O-乙酰基-2-叠氮基-3,4-二-O-苄基-2-脱氧-D-葡萄糖吡喃，这是合成葡萄糖胺寡糖的构建块。
• Metabolic labeling and molecular enhancement of biological materials using bioorthogonal reactions
  申请人：The General Hospital Corporation

  公开号：US20170362266A1

  公开（公告）日：2017-12-21

  The present application provides methods of functionalizing an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal or by culturing an organ or tissue in a bioreactor containing such nutrient. The present application also provides methods of selectively functionalizing extracellular matrix (ECM) of an organ or tissue of a mammal by administering a nutrient (e.g., peracetylated N-azido galactosamine Ac4GalNAz) to the mammal. In some aspects, the present application provides a decellularized scaffold of a mammalian organ or tissue comprising an extracellular matrix, wherein the extracellular matrix of the decellularized scaffold is functionalized with a chemical group that is reactive in a bioorthogonal chemical reaction, such as an azide chemical group. The present application also provides biological prosthetic mesh and mammalian organs and tissues for transplantation prepared according to the methods of the application.

  本申请提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）或在含有这种营养物质的生物反应器中培养器官或组织来功能化哺乳动物器官或组织的方法。本申请还提供了一种通过向哺乳动物投与营养物质（例如，乙酰化N-叠氮基半乳糖氨酸Ac4GalNAz）来选择性地功能化哺乳动物器官或组织的细胞外基质（ECM）的方法。在某些方面，本申请提供了哺乳动物器官或组织的脱细胞支架，其中脱细胞支架的细胞外基质被功能化为在生物正交化学反应中具有反应性的化学基团，例如叠氮基团。本申请还提供了根据本申请的方法制备的生物义肢网和哺乳动物器官和组织用于移植。