(2S,3S,4S,5R,6R)-6-(2-Acryloylamino-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester | 141520-84-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-6-(2-Acryloylamino-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 141520-84-5
• 化学式: C₁₂H₁₉NO₈
• 分子量: 305.285
• InChiKey: RBLQGBDLXZWUCW-GOVZDWNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.71
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  134.55
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-6-(2-Acryloylamino-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以89%的产率得到2-Acrylamidoethyl β-D-glucopyranosiduronic acid
  参考文献：
  名称：

  Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom

  摘要：

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

  DOI：

  10.1016/s0008-6215(00)90501-9
• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-6-(2-Azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal Dowex 1-X₈ (hco3^-) resin 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (2S,3S,4S,5R,6R)-6-(2-Acryloylamino-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of lysine-containing fragments of the Proteus mirabilis O27 O-specific polysaccharide and neoglyco- conjugates therefrom

  摘要：

  Amide-linked lysine mono- and di-uronic acid fragments of the O-specific polysaccharide from P. mirabilis O27 have been synthesised. N(epsilon)-Boc-L-lysine tert-butyl ester was condensed with 2-azidoethyl glycosides of glucuronic acid and beta-D-GlcpNAc-(1 --> 3)-beta-D-GlcpA. Transformation of the products into 2-acrylamidoethyl glycosides, followed by deprotection using trifluoroacetic acid, gave the target monomers that were converted into high-molecular-weight copolymer-type neoglycoconjugates.

  DOI：

  10.1016/s0008-6215(00)90501-9