allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside | 286476-64-0

• 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-3-O-allyloxycarbonyl-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-3-O-alloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,4-di-O-benzoyl-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-prop-2-enoxycarbonyloxyoxan-2-yl]oxy-5-benzoyloxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 286476-64-0
• 化学式: C₄₅H₄₅NO₁₇
• 分子量: 871.849
• InChiKey: DNSZJWJFXJWANH-GOWMYXEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  63
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  215
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-fucopyranoside 在 吗啉 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  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
• 作为产物：
  描述：

  allyl 2,4-di-O-benzoyl-α-L-fucopyranoside 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.67h， 生成 allyl (4,6-di-O-acetyl-3-O-allyloxycarbonyl-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

文献信息

• Model System for Cell Adhesion Mediated by Weak Carbohydrate–Carbohydrate Interactions
  作者：Bärbel Lorenz、Luis Álvarez de Cienfuegos、Marieelen Oelkers、Ella Kriemen、Christian Brand、Milena Stephan、Eva Sunnick、Deniz Yüksel、Venkateshwarlu Kalsani、Krishna Kumar、Daniel B. Werz、Andreas Janshoff

  DOI：10.1021/ja210304j

  日期：2012.2.22

  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.