methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside | 172603-69-9

• 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-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-5-azido-2,3-dimethoxy-4-[(4-methoxyphenyl)methoxy]-6-methyloxane
• CAS: 172603-69-9
• 化学式: C₁₆H₂₃N₃O₅
• 分子量: 337.376
• InChiKey: SHBGQDSOSKDGEP-DMHMKPBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-α-D-mannopyranoside 在 吡啶 、 硫化氢 、 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 为溶剂， 反应 4.0h， 生成 methyl 4-amino-4,6-dideoxy-2-O-methyl-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
• 作为产物：
  描述：

  甲基 4-叠氮基-4,6-二脱氧吡喃甘露糖苷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-2-O-methyl-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 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.