methyl 4,6-dideoxy-4-[(2S)-2,4-dihydroxybutanamido]-2-O-methyl-alpha-D-mannopyranoside | 172603-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-dideoxy-4-[(2S)-2,4-dihydroxybutanamido]-2-O-methyl-alpha-D-mannopyranoside
• 英文别名: (2S)-2,4-dihydroxy-N-[(2R,3S,4S,5S,6S)-4-hydroxy-5,6-dimethoxy-2-methyloxan-3-yl]butanamide
• CAS: 172603-73-5
• 化学式: C₁₂H₂₃NO₇
• 分子量: 293.317
• InChiKey: NGGZJRAGGXAXNO-RPBIHCLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4,6-dideoxy-4-[(2S)-2,4-dihydroxybutanamido]-2-O-methyl-alpha-D-mannopyranoside 在 吡啶 、 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 3-O-benzoyl-4-(2-O-benzoyl-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Some Analogs of the Methyl α-Glycoside of the Presumed Antigenic Determinant of the O-Specific Polysaccharide ofVibrio choleraeO:1, Serotype Ogawa

  摘要：

  The following analogs of the title determinant, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, have been prepared: methyl 3,4,6,-trideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(4-hydroxybutyramido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3,4-dideoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3-deoxy-D-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(2-deoxy-L-glycero-tetronamido)2-O-methyl-alpha-D-mannopyranoside, methyl 4-acetamido-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside, methyl 4,6-dideoxy-4-(3 -deoxy-L-glycero-tetronamido)-2-O-ethyl-alpha-D-mannopyranoside, and methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-propyl-alpha-D-mannopyranoside.

  DOI：

  10.1080/07328309808002896
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 在 吡啶 、 sodium hydroxide 、 lactone C₄H₆O₃ 、 硫化氢 、 四丁基溴化铵 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 methyl 4,6-dideoxy-4-[(2S)-2,4-dihydroxybutanamido]-2-O-methyl-alpha-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and crystal structure of methyl 4,6-dideoxy-4-(3-deoxy-l-glycero-tetronamido) - 2-O-methyl-α-d-mannopyranoside, the methyl α-glycoside of the terminal unit, and presumed antigenic determinant, of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  Methyl 4-azido-4,6-dideoxy-3-O-benzyl-alpha-D-mannopyranoside and its analogous 3-O-(4-methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were converted into methyl 4-amino-4,6-dideoxy-2-O-methyl-alpha-D-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolactone gave the methyl glycoside of 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-2-O-methyl-alpha-D-mannopyranose, the monosaccharide that is reported to be the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Ogawa. The unit cell packing of the compound, which crystallized as a monohydrate, differs from that of the previously described crystalline compound lacking the 2-O-methyl group. The unmethylated sugar is the terminal moiety of the O-specific polysaccharide of Vibrio cholerae 0:1, serotype Inaba. The crystal structure of methyl 4,6-dideoxy-2-0-methyl-4-trifluoroacetamido-alpha-D-mannopyranoside is also described.

  DOI：

  10.1016/0008-6215(95)00147-l

文献信息

• Synthesis of the methyl α-glycosides of a di-, tri-, and a tetra-saccharide fragment mimicking the terminus of the O-polysaccharide of Vibrio cholerae 0:1, serotype Ogawa
  作者：Ping-sheng Lei、Yuji Ogawa、Pavol Kováč

  DOI：10.1016/0008-6215(95)00331-2

  日期：1996.2

  )-4,6- dideoxy-alpha-D-mannopyranoside (4) gave the fully acetylated disaccharide 5, which was deacetylated yielding the methyl alpha-glycoside of title disaccharide. The disaccharide glycosyl donor required for the blockwise synthesis of the title tri- and the tetra-saccharide, 3-O-acetyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronamido)-4,6-d ideoxy-2-O- methyl-alpha-D-mannopyranosyl-(1-->2)-3-O-acetyl-4-

  将甲基4-（3-脱氧-L-甘油-四氢酰胺基）-4,6-二脱氧-2-O-甲基-α-D-甘露吡喃糖苷乙酰化，并用二氯甲基甲基醚-ZnCl2处理完全保护的甲基糖苷（ DCMME-ZnCl2）试剂可生成3-O-乙酰基-4-（2,4-二-O-乙酰基-3-脱氧-L-甘油-四氢酰胺基）-4,6-二脱氧-2-O-甲基-α -D-甘露聚糖氰基氯（3）。3与甲基3-O-乙酰基-4-（2,4-二-O-乙酰基-3-脱氧-L-甘油-四氢酰胺基）-4,6-二脱氧-α-D-甘露吡喃糖苷的缩合反应（4）完全乙酰化的二糖5，其被脱乙酰化，得到标题二糖的甲基α-糖苷。标题三糖和四糖3-O-乙酰基-4-（2,4-二-O-乙酰基-3-脱氧-L-甘油-四氢酰胺基）的嵌段合成所需的二糖糖基供体4,6-d ideoxy-2-O-methyl-alpha-D-mannopyranosyl-（1-> 2）-3-O-acetyl-4-（2，
• Conjugate Vaccines from Bacterial Antigens by Squaric Acid Chemistry: A Closer Look
  作者：Peng Xu、Meagan Kelly、Willie F. Vann、Firdausi Qadri、Edward T. Ryan、Pavol Kováč

  DOI：10.1002/cbic.201600699

  日期：2017.4.18

  polysaccharides to proteins by using squarate chemistry shows a twofold increase in conjugation efficiency. The spent reagent can be regenerated, and the conjugate vaccine made from the conjugation reagent is comparable with the vaccine made from the parent antigen. CP: carrier protein; OSPc: O‐SP–core.

  公平公正：利用方形化学将脱脂细菌多糖与蛋白质缀合的新方案显示缀合效率提高了一倍。用过的试剂可以再生，用该结合试剂制成的结合疫苗与用亲本抗原制成的疫苗具有可比性。CP：载体蛋白；OSPc：O-SP-核心。