8-(Methoxycarbonyl)octyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside | 146194-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-(Methoxycarbonyl)octyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-D-mannopyranoside
• 英文别名: methyl 9-[(2S,3S,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxynonanoate
• CAS: 146194-30-1
• 化学式: C₂₄H₄₃NO₁₃
• 分子量: 553.604
• InChiKey: RTQLLTBBLUXYKB-QJOAWPRHSA-N

物化性质

• 沸点：
  800.5±65.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 在 palladium on activated charcoal 甲醇 、 silver silicate 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 乙酸肼 作用下， 以 甲醇 、 苯 为溶剂， 生成 8-(Methoxycarbonyl)octyl 6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-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

文献信息

• Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates
  作者：Tamio Sugawara、Kunihiko Irie、Hiroyuki Iwasawa、Takayoshi Yoshikawa、Satoshi Okuno、Hiroshi K. Watanabe、Takashi Kato、Mitsuru Shibukawa、Yukio Ito

  DOI：10.1016/s0008-6215(00)90517-2

  日期：1992.6

  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.