methyl 4-azido-4,6-dideoxy-2-O-(4-methoxybenzyl)-α-D-mannopyranoside | 172603-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-azido-4,6-dideoxy-2-O-(4-methoxybenzyl)-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5S,6R)-5-azido-2-methoxy-3-[(4-methoxyphenyl)methoxy]-6-methyloxan-4-ol
• CAS: 172603-67-7
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: OIMGGFWHUBDRLN-FCHWROMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-4,6-dideoxy-2-O-(4-methoxybenzyl)-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 光气 、 sodium tetrahydroborate 、 二乙胺基三氟化硫 、 氢气 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.0h， 生成 methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  合成探索D-过胺的3-脱氧-3-氟衍生物。

  摘要：

  根据文献的先例，尝试了通过4-甲基叠氮基-2-O-苄基-4的氟化制备甲基4-叠氮基-3,4,6-三苯氧基-3-氟代-α-D-甘露吡喃糖苷（18）。 ，6-二脱氧-α-D-altropyranoside与二乙基氨基三氟化硫（DAST）。与预期相反，该反应在氟化位点处保持构型发生，从而产生甲基4-叠氮基-2-O-苄基-3,4,6-三苯氧基-3-氟代-α-D-萘并吡喃糖苷。用DAST处理甲基4-叠氮基-2-O-苄基-4,6-二脱氧-α-D-阿洛吡喃糖苷（8）或其2-（对甲氧基苄基）类似物9导致氟化反应，位置上的构型反转如图3所示，分别得到相应的3-脱氧-3-氟吡喃葡萄糖苷10和11。因此，化合物11由11通过在O-2处进行对-甲氧基苄基化而制备，然后在所得的甲基4-叠氮基-3,4,6-三苯氧基-3-氟-α-D-吡喃葡萄糖苷中的C-2处的构型反转。18（19）的2-O-甲基类似物是通过18的甲基化

  DOI：

  10.1016/s0008-6215(01)00188-4
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 、 4-甲氧基氯苄 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以13%的产率得到Methyl 4-azido-4,6-dideoxy-2,3-di-O-4-methoxybenzyl-α-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-glycoside of a trisaccharide mimicking the terminus of the O antigen of Vibrio cholerae O:1, serotype Inaba
  作者：Ping-sheng Lei、Yuji Ogawa、Pavol Kováč

  DOI：10.1016/0008-6215(95)00281-2

  日期：1995.12

  Coupling of methyl 4-amino-4,6-dideoxy-2-O-4-methoxybenzyl-alpha-D-mannopyranoside, obtained from the corresponding 4-azido derivative by treatment with H2S, with 3-deoxy-L-glycero-tetronolactone gave the crystalline methyl 4-(3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-4-methoxybenzyl- alpha-D- mannopyranoside (7). Subsequent acetylation of 7, followed by O-demethoxybenzylation of the 8 formed

  通过用H2S处理从相应的4-叠氮基衍生物获得的4-氨基-4,6-二脱氧-2-O-4-甲氧基苄基-α-D-甘露吡喃甲基与3-脱氧-L-甘油-四氢内酯的偶联得到结晶的甲基4-（3-脱氧-L-甘油-四氢酰胺基）-4，6-二脱氧-2-O-4-甲氧基苄基-α-D-甘露吡喃糖苷（7）。随后进行7的乙酰化，然后对8进行O-脱甲氧基苄基化，得到结晶的甲基3-O-乙酰基-4,6-二脱氧-4-（2,4-二-O-乙酰基-3-脱氧-L-甘油-tetronami do）-alpha- D-mannopyranoside（9），用作标题三糖构建中的关键中间体。为了制得允许在O-2处寡糖链延伸的糖基供体，通过常规转化将化合物9转化为3-O-乙酰基-2-O-溴乙酰基-4,6-二脱氧-4-（2，4-二-O-乙酰基-3-脱氧-L-葡萄糖基-四氢氨基氨基）-α-D-甘露吡喃糖基氯（12）。12与9的缩合得到二糖20，其在O-2
• Synthetic explorations towards 3-deoxy-3-fluoro derivatives of d-perosamine
  作者：Emmanuel Poirot、Alex H.C Chang、Derek Horton、Pavol Kováč

  DOI：10.1016/s0008-6215(01)00188-4

  日期：2001.8

  6-dideoxy-alpha-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O-benzyl-3,4,6-trideoxy-3-fluoro-alpha-D-altropyranoside. Treatment with DAST of methyl 4-azido-2-O-benzyl-4,6-dideoxy-alpha-D-allopyranoside (8), or its 2-(p-methoxybenzyl) analog 9 resulted

  根据文献的先例，尝试了通过4-甲基叠氮基-2-O-苄基-4的氟化制备甲基4-叠氮基-3,4,6-三苯氧基-3-氟代-α-D-甘露吡喃糖苷（18）。 ，6-二脱氧-α-D-altropyranoside与二乙基氨基三氟化硫（DAST）。与预期相反，该反应在氟化位点处保持构型发生，从而产生甲基4-叠氮基-2-O-苄基-3,4,6-三苯氧基-3-氟代-α-D-萘并吡喃糖苷。用DAST处理甲基4-叠氮基-2-O-苄基-4,6-二脱氧-α-D-阿洛吡喃糖苷（8）或其2-（对甲氧基苄基）类似物9导致氟化反应，位置上的构型反转如图3所示，分别得到相应的3-脱氧-3-氟吡喃葡萄糖苷10和11。因此，化合物11由11通过在O-2处进行对-甲氧基苄基化而制备，然后在所得的甲基4-叠氮基-3,4,6-三苯氧基-3-氟-α-D-吡喃葡萄糖苷中的C-2处的构型反转。18（19）的2-O-甲基类似物是通过18的甲基化
• 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
  作者：Ping-sheng Lei、Yuji Ogawa、Judith L. Flippen-Anderson、Pavol Kováĉ

  DOI：10.1016/0008-6215(95)00147-l

  日期：1995.9

  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.