8-(Methoxycarbonyl)octyl 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 143528-62-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-(Methoxycarbonyl)octyl 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: methyl 9-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-[[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxynonanoate
• CAS: 143528-62-5
• 化学式: C₇₁H₈₂O₁₃
• 分子量: 1143.42
• InChiKey: LHSLDXALRVSPPU-HEVCUNLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  84.0
• 可旋转键数：
  35.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  127.83
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  8-(Methoxycarbonyl)octyl 6-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以47%的产率得到8-(Methoxycarbonyl)octyl 6-O-(α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates

  摘要：

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.

  DOI：

  10.1016/s0008-6215(00)90517-2
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl chloride 、 8-(Methoxycarbonyl)octyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以27.3%的产率得到8-(Methoxycarbonyl)octyl 6-O-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates

  摘要：

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.

  DOI：

  10.1016/s0008-6215(00)90517-2