allyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->6)-[(2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)]-4-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside | 213913-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->6)-[(2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)]-4-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetyloxy-2-[[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxymethyl]-5-(1,3-dioxoisoindol-2-yl)-6-prop-2-enoxyoxan-4-yl]oxy-2-(hydroxymethyl)-4,5-bis[(4-methylbenzoyl)oxy]oxan-3-yl] 4-methylbenzoate
• CAS: 213913-19-0
• 化学式: C₆₉H₆₈N₂O₂₅
• 分子量: 1325.3
• InChiKey: CKOWGEWCJNMNEN-GJJCADGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  96
• 可旋转键数：
  29
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  335
• 氢给体数：
  1
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  allyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->6)-[(2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)]-4-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 重铬酸吡啶 、 4 A molecular sieve 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 170.0h， 生成 3-(2-Aminoethylthio)propyl (2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes

  摘要：

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00125-6
• 作为产物：
  描述：

  allyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->6)-[(6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)]-4-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 在 乙酸肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 以91%的产率得到allyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->6)-[(2,3,4-tri-O-p-toluoyl-β-D-glucopyranosyl)-(1->3)]-4-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes

  摘要：

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00125-6