allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside | 286476-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
• 英文别名: allyl 4,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-α-L-fucopyranoside；[(2S,3R,4R,5S,6R)-4-[(2S,3R,4R,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)-4-hydroxyoxan-2-yl]oxy-5-benzoyloxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 286476-65-1
• 化学式: C₄₁H₄₁NO₁₅
• 分子量: 787.774
• InChiKey: QPXBJAZUVAMAKX-IRLBKICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  57
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  200
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside 在 三甲基铵三氧化硫共聚物 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 48.5h， 以75%的产率得到allyl (sodium 4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl 3-sulfate)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Model System for Cell Adhesion Mediated by Weak Carbohydrate–Carbohydrate Interactions

  摘要：

  The multivalent carbohydrate-carbohydrate interaction between membrane-anchored epitopes derived from the marine sponge Microciona prolifera has been explored by colloidal probe microscopy. An in situ coupling of sulfated and non-sulfated disaccharides to membrane-coated surfaces was employed to mimic native cell cell contacts. The dynamic strength of the homomeric self-association was measured as a function of calcium ions and loading rate. A deterministic model was used to estimate the basic energy landscape and number of participating bonds in the contact zone.

  DOI：

  10.1021/ja210304j
• 作为产物：
  描述：

  Benzoic acid (3aR,4S,6R,7S,7aR)-6-allyloxy-4-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 在 吗啉 、 吡啶 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.92h， 生成 allyl (4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside
  参考文献：
  名称：

  Synthesis and conjugation of a sulfated disaccharide involved in the aggregation process of the marine sponge Microciona prolifera

  摘要：

  The synthesis is reported of allyl (sodium 2-acetamido-2-deoxy-beta-D-glucopyranosyl 3-sulfate)-(1-->3)-alpha-L-fucopyranoside which represents an oligosaccharide fragment of the aggregation factor of the marine sponge Microciona prolifera. The title compound was obtained by coupling of 3-O-allyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with allyl 2,4-di-O-benzoyl-alpha-Lfucopyranoside, followed by de-isopropylidenation, acetylation, de-allyloxycarbonylation, sulfation, de-acylation, and finally N-acetylation. The allyl glycoside was eventually converted into a 3-(2-aminoethylthio)propyl glycoside and then coupled to bovine serum albumin (BSA) using diethyl squarate as the bivalent linker, yielding 8 hapten molecules per molecule of BSA. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00585-6