methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-α-D-mannopyranoside | 172603-68-8

• 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)-α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-4-(4-methoxybenzyloxy)-5-azidotetrahydro-2-methoxy-6-methyl-2H-pyran-3-ol；(2S,3S,4S,5R,6R)-5-azido-2-methoxy-4-[(4-methoxyphenyl)methoxy]-6-methyloxan-3-ol
• CAS: 172603-68-8
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: LSCALEMXPANMFB-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-3-O-(4-methoxybenzyl)-α-D-mannopyranoside 在 吡啶 、 sodium hydroxide 、 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 、 二甲基亚砜 为溶剂， 反应 7.0h， 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 、 4-甲氧基溴苄 在 二正丁基氧化锡 、 四丁基碘化铵 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以93%的产率得到methyl 4-azido-4,6-dideoxy-3-O-(4-methoxybenzyl)-α-D-mannopyranoside
  参考文献：
  名称：

  从头不对称合成炭疽四糖及相关四糖

  摘要：

  从乙酰呋喃已经开发出从天然产物炭疽四糖1和具有异头己基叠氮化物基团的类似物2的不对称方法。四糖的构建是通过传统的[3 +1]糖基化策略实现的。迭代非对映选择性钯催化糖基化，luche还原反应，非对映选择性二羟基化，选择性和区域选择性酰化物用于该组装升-鼠李糖-trisaccharide构建块。除Luche还原和二羟基化作用外，蒽酮构建基块还需要钯催化的叠氮化物烯丙基化和三氟甲磺酸酯转化来设定葡萄糖立体化学。

  DOI：

  10.1021/jo800691v

文献信息

• De Novo Asymmetric Synthesis of Anthrax Tetrasaccharide and Related Tetrasaccharide
  作者：Haibing Guo、George A. O’Doherty

  DOI：10.1021/jo800691v

  日期：2008.7.1

  A de novo asymmetric approach to the natural product anthrax tetrasaccharide 1 and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective

  从乙酰呋喃已经开发出从天然产物炭疽四糖1和具有异头己基叠氮化物基团的类似物2的不对称方法。四糖的构建是通过传统的[3 +1]糖基化策略实现的。迭代非对映选择性钯催化糖基化，luche还原反应，非对映选择性二羟基化，选择性和区域选择性酰化物用于该组装升-鼠李糖-trisaccharide构建块。除Luche还原和二羟基化作用外，蒽酮构建基块还需要钯催化的叠氮化物烯丙基化和三氟甲磺酸酯转化来设定葡萄糖立体化学。
• 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.