methyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-glucopyranoside | 942043-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-glucopyranoside
• 英文别名: benzoic acid 4,5-bis-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester；[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-2-methoxy-4,5-bis(phenylmethoxy)oxan-3-yl] benzoate
• CAS: 942043-19-8
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: UAYGLVUYMCGHAV-CBNWRBMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-glucopyranoside 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Targeting the Delivery of Glycan-Based Paclitaxel Prodrugs to Cancer Cells via Glucose Transporters

  摘要：

  This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2'-paclitaxel and the 2'-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective cytotoxicity against cancer cell lines, but showed reduced toxicity toward normal cell lines and cancer cell lines with low expression levels of GLUTs. The ester conjugated prodrug 1 showed the most cytotoxicity among the prodrugs examined and could be transported into cells via GLUTs. Fluorescent and confocal microscopy demonstrated that targeted cells exhibited morphological changes in tubulin and chromosomal alterations that were similar to those observed with paclitaxel treatment. Therefore, these glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs.

  DOI：

  10.1021/jm8006257
• 作为产物：
  描述：

  methyl 2-O-benzoyl-3-O-benzyl (R)-4,6-O-benzylidene-α-D-glucopyranoside 在 aluminum (III) chloride 、 Triethyl-amine; compound with trifluoroborane 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.33h， 以74.5%的产率得到methyl 2-O-benzoyl-3,4-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Targeting the Delivery of Glycan-Based Paclitaxel Prodrugs to Cancer Cells via Glucose Transporters

  摘要：

  This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2'-paclitaxel and the 2'-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective cytotoxicity against cancer cell lines, but showed reduced toxicity toward normal cell lines and cancer cell lines with low expression levels of GLUTs. The ester conjugated prodrug 1 showed the most cytotoxicity among the prodrugs examined and could be transported into cells via GLUTs. Fluorescent and confocal microscopy demonstrated that targeted cells exhibited morphological changes in tubulin and chromosomal alterations that were similar to those observed with paclitaxel treatment. Therefore, these glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs.

  DOI：

  10.1021/jm8006257

文献信息

• METHOD FOR PREPARING HEXOSE DERIVATIVES
  申请人：Hung Shang Cheng

  公开号：US20090105466A1

  公开（公告）日：2009-04-23

  A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

  制备己糖衍生物的方法包括以下步骤：提供硅烷基化的己糖，将硅烷基化的己糖与第一羰基化合物在催化剂存在下处理，形成缩酮化的己糖，将缩酮化的己糖与第二羰基化合物处理后，再用第一还原剂处理，形成醚化的己糖，并将醚化的己糖转化为目标己糖衍生物，可以是2-醇己糖、3-醇己糖、4-醇己糖或6-醇己糖。具体来说，本发明可以采用高度选择性的方案制备己糖衍生物，以保护单糖单元的各个羟基，并以一锅法安装正交保护基图案。
• Synthesis of β‐Glucosides with 3‐ <i>O</i> ‐Picoloyl‐Protected Glycosyl Donors in the Presence of Excess Triflic Acid: Defining the Scope
  作者：Michael P. Mannino、Alexei V. Demchenko

  DOI：10.1002/chem.201905278

  日期：2020.3.2

  Excellent β-stereoselectivity for the glycosylation with glucosyl donors equipped with the 3-O-picoloyl (Pico) group, without the use of participating group, was achieved in the presence of NIS/excess TfOH promoter system. A complete investigation of the scope of this reaction was performed, revealing all important attributes of successful glycosylation. While altering the halogen source was tolerated

  在存在NIS /过量TfOH启动子系统的情况下，在不使用参与基团的情况下，对于配备有3-O-picoloyl（Pico）基团的葡萄糖基供体的糖基化具有出色的β-立体选择性。对该反应范围进行了全面研究，揭示了成功糖基化的所有重要属性。在容忍改变卤素源的同时，三氟甲磺酸根阴离子的取代导致立体选择性的完全丧失。经确定，Pico基团的质子化在该反应中至关重要。还发现质子化吡啶环的稳定性或程度是获得高立体选择性的另一个重要关键因素。发现受体的亲核性与所获得的立体选择性成正比，暗示了类似于SN 2的机制。
• Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine–aluminium chloride reagent
  作者：Katalin Daragics、Pál Szabó、Péter Fügedi

  DOI：10.1016/j.carres.2011.04.046

  日期：2011.9

  Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-D-glucopyranosides with BH(3).NMe(3)-AlCl(3) are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was rationalized by aluminium chelate formation between the O-4 acetal and the benzoyl carbonyl group oxygens. It was also shown that these side reactions can be eliminated by using

  3-O-苯甲酰基-4,6-O-亚苄基-D-吡喃葡萄糖苷与BH（3）.NMe（3）-AlCl（3）的还原性开环伴随有副反应，例如脱苯甲酰化和苯甲酸酯的还原苯甲基醚。通过在O-4乙缩醛和苯甲酰基羰基氧之间形成铝螯合物，可以合理地解释这种现象。还显示可以通过使用BH（3）.THF作为还原剂消除这些副反应。
• Targeting the Delivery of Glycan-Based Paclitaxel Prodrugs to Cancer Cells via Glucose Transporters
  作者：Yih-Shyan Lin、Rudeewan Tungpradit、Supachok Sinchaikul、Feng-Ming An、Der-Zen Liu、Suree Phutrakul、Shui-Tein Chen

  DOI：10.1021/jm8006257

  日期：2008.12.11

  This report describes the synthesis of four novel paclitaxel based prodrugs with glycan conjugation (1-4). Glycans were conjugated using an ester or ether bond as the linker between 2'-paclitaxel and the 2'-glucose or glucuronic acid moiety. These prodrugs showed good water solubility and selective cytotoxicity against cancer cell lines, but showed reduced toxicity toward normal cell lines and cancer cell lines with low expression levels of GLUTs. The ester conjugated prodrug 1 showed the most cytotoxicity among the prodrugs examined and could be transported into cells via GLUTs. Fluorescent and confocal microscopy demonstrated that targeted cells exhibited morphological changes in tubulin and chromosomal alterations that were similar to those observed with paclitaxel treatment. Therefore, these glycan-based prodrugs may be good drug candidates for cancer therapy, and the glycan conjugation approach is an alternative method to enhance the targeted delivery of other drugs to cancer cells that overexpress GLUTs.