3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate | 208047-70-5

• 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: 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
• 英文别名: 3,6-di-O-benzyl-2-deoxy-4-O-levulinyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate；3,6-di-O-benzyl-4-O-levulinoyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate；[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] 4-oxopentanoate
• CAS: 208047-70-5
• 化学式: C₃₅H₃₃Cl₃N₂O₉
• 分子量: 732.014
• InChiKey: GOCYGPYUUDLXJO-JGZOBPLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 一水合肼 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Solvent Effect in Glycosylation Reaction on Polymer Support

  摘要：

  研究了聚合物支持物上糖基化反应的溶剂效应。在 CH3CN 的存在下，δ 产物增加。

  DOI：

  10.1055/s-1998-1750
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids

  摘要：

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00295-1

文献信息

• Preparation of Thiosugars and Their Use
  申请人：Davis Benjamin Guy

  公开号：US20090176970A1

  公开（公告）日：2009-07-09

  A process for the preparation of a thiosaccharide represented by Saccharide-S-H wherein Saccharide comprises at least 4 sugar units, comprises subjecting a corresponding compound of the formula (P)Saccharide-S-(P) wherein (P) represents an O- or S-protecting group(s), to Birch reduction.

  一种制备由糖硫代糖（Saccharide-S-H）表示的硫代糖的方法，其中糖代表至少4个糖单元，包括将具有以下结构的相应化合物（P）糖硫代糖（P）进行桦还原：（P）糖硫代糖（P），其中（P）代表一个或多个O-或S-保护基。
• Automated Synthesis of Oligosaccharides
  作者：Emma R. Palmacci、Obadiah J. Plante、Michael C. Hewitt、Peter H. Seeberger

  DOI：10.1002/hlca.200390331

  日期：2003.12

  The chemical synthesis of oligosaccharides with an automated solid-phase synthesizer is described. An octenediol linker served to attach the growing oligosaccharide chain to the solid support, and the desired structures were cleaved from the support via olefin metathesis to afford a pentenyl glycoside. The automated syntheses of several important carbohydrates, including a pentarhamnoside, a proteoglycan

  描述了用自动固相合成仪化学合成寡糖。辛烯二醇接头用于将增长的寡糖链连接至固体载体，并且通过烯烃复分解从载体上裂解所需的结构，从而得到戊烯基糖苷。几种重要碳水化合物的自动化合成，以较高的总收率和大约20％的产率完成，其中包括戊糖甙，蛋白聚糖连接区四糖，植物抗毒素引发剂十二糖和支链利什曼原虫脂磷酸聚糖四糖。比溶液阶段方法快20倍。
• Monitoring Glycan–Protein Interactions by NMR Spectroscopic Analysis: A Simple Chemical Tag That Mimics Natural CH–π Interactions
  作者：Luis P. Calle、Begoña Echeverria、Antonio Franconetti、Sonia Serna、M. Carmen Fernández‐Alonso、Tammo Diercks、F. Javier Cañada、Ana Ardá、Niels‐Christian Reichardt、Jesús Jiménez‐Barbero

  DOI：10.1002/chem.201501248

  日期：2015.8.3

  propose the difluoroacetamide moiety (an acetamide bioisoster) as a novel tag for detecting by NMR analysis those glycan–protein interactions that involve N‐acetylated sugars. Although difluoroacetamide has been used previously as a substituent in medicinal chemistry, here we employ it as a specific sensor to monitor interactions between GlcNAc‐containing glycans and a model lectin (wheat germ agglutinin)

  分子识别过程的检测需要鲁棒，特定且易于实现的传感方法，尤其是对于筛选应用。在这里，我们提出了二氟乙酰胺部分（乙酰胺生物甾醇）作为一种新型标签，用于通过NMR分析检测涉及N-乙酰化糖类的糖蛋白相互作用。尽管二氟乙酰胺以前曾在药物化学中用作取代基，但在这里我们将其用作监测含GlcNAc的聚糖与模型凝集素（小麦胚芽凝集素）之间相互作用的特异传感器。与广泛使用的三氟乙酰胺基相反，二氟乙酰胺标签包含双子1 H和19 F原子，允许1 H和19F NMR方法可轻松，可靠地检测涉及一系列结合亲和力的GlcNAc-（或GalNAc-）部分的分子识别过程。CHF 2 CONH-部分的行为与所涉及的芳族糖相互作用中的天然乙酰胺片段非常相似，提供相似的结合能和构象，而全氟化CF 3 CONH-类似物的区别则更大。
• Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids
  作者：Isao Ohtsuka、Noriyasu Hada、Mutsumi Sugita、Tadahiro Takeda

  DOI：10.1016/s0008-6215(02)00295-1

  日期：2002.11

  Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar. have quite unique structures containing GlcNAcbeta-(1-->3)-Man and GalNAcbeta-(1-->4)-GlcNAcbeta-(1-->3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1--> 3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1-->1)-Cer and beta-D-GalNAcp-(1-->4)-beta-D-GlcNAcp-(1-->3)-beta-D-Manp-(1-->4)-beta-D-Glcp-(1--> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Solvent Effect in Glycosylation Reaction on Polymer Support
  作者：Shino Manabe、Yukishige Ito、Tomoya Ogawa

  DOI：10.1055/s-1998-1750

  日期：1998.6

  The solvent effect in glycosylation reaction on polymer support was investigated. In the presence of CH3CN, the β product was increased.

  研究了聚合物支持物上糖基化反应的溶剂效应。在 CH3CN 的存在下，δ 产物增加。