6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate | 144367-26-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(4-Me)(-2)[Bz(4-Me)(-3)][Bz(4-Me)(-4)][levulinoyl(-6)]Glc(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-4,5-bis[(4-methylbenzoyl)oxy]-2-(4-oxopentanoyloxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 4-methylbenzoate
• CAS: 144367-26-0
• 化学式: C₃₇H₃₆Cl₃NO₁₁
• 分子量: 777.052
• InChiKey: CGWRHUMPXLCGHL-QVCIFTRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  165
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 草酰氯 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 乙酸肼 、 对甲苯磺酸 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 甲胺 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 反应 69.34h， 生成 3-(2-Aminoethylthio)propyl (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：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 三乙烯二胺 、 ammonium cerium(IV) nitrate 、 2-氯-1-甲基吡啶碘化物 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 吡啶 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 10.33h， 生成 6-O-levulinoyl-2,3,4-tri-O-p-toluoyl-α-D-glucopyranosyl trichloroacetimidate
  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

文献信息

• Synthesis and conjugation of oligosaccharide fragments related to the immunologically reactive part of the circulating anodic antigen of the parasite Schistosoma mansoni
  作者：Henricus J. Vermeer、Koen M. Halkes、J. Albert van Kuik、Johannis P. Kamerling、Johannes F. G. Vliegenthart

  DOI：10.1039/b002083o

  日期：——

  l (2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→6)-[(β-D-glucopyranosyluronic acid)-(1→3)]-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→6)-[(β-D-glucopyranosyluronic acid)-(1→3)]-2-acetamido-2-deoxy-β-D-galactopyranoside, is described. Moreover, 1-O-[3-(2-aminoethylthio)propyl]-N-acetyl-β-D-galactosamine was synthesized. Oxidation steps in the synthesis of tri- to pentasaccharide CAA fragments were

  循环阳极的免疫反应部分 抗原从寄生虫（CAA）曼氏血吸虫是一个苏氨酸链接 多糖由→6）-[β- D -Glc p A-（1→3）]-β- D- Gal p NAc-（1→重复组成二糖。在免疫化学项目的框架内，作为早期合成二四糖CAA片段，含间隔物的五糖片段的合成，3-（2-氨基乙硫基）丙基（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）酸）-（1→3）]-（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）-（1→3）]-2描述了-乙酰氨基-2-脱氧-β - D-吡喃半乳糖苷。此外，合成了1- O- [3-（2-氨基乙硫基）丙基] -N-乙酰基-β - D-半乳糖胺。氧化作用 三元合成的步骤 五糖 使用重铬酸吡啶鎓和 醋酸酐。TEMPO催化的氧化反应在合成中得到了探索。1 - O- [6-氨基己基]-β-
• Synthesis and conjugation of oligosaccharide analogues of fragments of the immunoreactive glycan part of the circulating anodic antigen of the parasite Schistosoma mansoni
  作者：Adriana Carvalho de Souza、Joeri Kuil、C. Elizabeth P. Maljaars、Koen M. Halkes、Johannes F. G. Vliegenthart、Johannis P. Kamerling

  DOI：10.1039/b410241j

  日期：——

  fragments of the CAA glycan. To generate information on the molecular level about the glycan specificity of the relevant IgM MAbs, two series of oligosaccharides related to the CAA disaccharide epitope were synthesized, and coupled to BSA. The first three analogues, beta-D-GlcpA-(1-->3)-[small beta]-D-GlcpNAc-(1-->O), beta-D-GlcpNAc-(1-->6)-[beta-D-GlcpA-(1-->3)]-beta-D-GlcpNAc-(1-->O), and beta-D-Glcp

  肠道相关循环阳极抗原（CAA）是由寄生虫曼氏血吸虫产生的主要排泄性抗原之一。CAA的免疫反应性部分是苏氨酸连接的多糖，由长段独特重复的二糖组成-> 6）-[β-D-GlcpA-（1-> 3）]-β-D-GalpNAc-（1 ->。以前，使用表面等离振子共振和ELISA技术已经显示，某些抗CAA IgM单克隆抗体（MAbs）也可以识别一系列牛血清白蛋白（BSA）偶联的合成二到五为了产生有关相关IgM MAb的聚糖特异性的分子水平信息，合成了与CAA二糖表位相关的两个系列寡糖，并与BSA偶联，前三个类似物β-D -GlcpA-（1-> 3）-[小beta] -D-GlcpNAc-（1-> O），beta-D-GlcpNAc-（1-> 6）-[beta-D-GlcpA-（1-> 3）]- beta-D-GlcpNAc-（1-> O）和beta-D-GlcpNA-（1-> 3）-beta-D-GlcpNAc-（1->
• Synthesis of hyaluronic acid-related di-, tri-, and tetra-saccharides having an N-acetylglucosamine residue at the reducing end
  作者：Ted M. Slaghek、Yoshiaki Nakahara、Tomoya Ogawa、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/s0008-6215(00)90971-6

  日期：1994.3

  The synthesis is reported of 4-methoxyphenyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (1), 4-methoxyphenyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-O-(beta-D- glucopyranosyluronic acid)-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (5), and 4-methoxyphenyl O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-(2-acetamido-2-deoxy-beta-D-glu

  据报道合成了4-甲氧基苯基O-（β-D-吡喃葡萄糖基糖醛酸）-（1→3）-2-乙酰氨基-2-脱氧β-D-吡喃葡萄糖苷（1），4-甲氧基苯基O-（ 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-（1-> 4）-O-（β-D-葡萄糖基吡喃糖醛酸）-（1-> 3）-2-乙酰氨基-2-脱氧- β-D-吡喃葡萄糖苷（5）和4-甲氧基苯基O-（β-D-吡喃葡萄糖基糖醛酸）-（1-> 3）-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）- （1-> 4）-O-（β-D-吡喃葡糖基糖醛酸）-（1-> 3）-2-乙酰氨基-2-脱氧-β-D-吡喃葡糖苷（10）细胞外多糖透明质酸。将6-O-Levulinoyl-2,3,4-三-Op-甲苯甲酰基-α-D-吡喃葡萄糖基三氯乙酰亚胺酸酯（3）与4-甲氧基苯基2-deoxy-4,6-O-isopropylidene-2-phthalimido-beta缩合-D-吡喃葡萄糖苷（4）。
• Stereocontrolled synthesis of hyaluronan tetrasaccharide
  作者：Ted Slaghek、Yoshiaki Nakahara、Tomoya Ogawa

  DOI：10.1016/s0040-4039(00)61248-0

  日期：1992.8

  A stereocontrolled synthesis of hyaluronan tetrasaccharide is described for th