6-O-(triphenylmethyl)-α-D-glucopyranosyl-6'-O-(triphenylmethyl)-α-D-glucopyranoside | 50705-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 6-O-(triphenylmethyl)-α-D-glucopyranosyl-6'-O-(triphenylmethyl)-α-D-glucopyranoside
• 英文别名: 6,6′-di-O-trityl-α,α′-trehalose；6,6'-di-O-triphenylmethyl-α,α-trehalose；6,6’-di-O-trityl-α,α'-trehalose；6,6'-di-(trityloxy)-α,α-trehalose；6,6'-Bis(triphenylmethyl)-α-D-trehalose；6,6'-di-O-trityl-α,α-trehalose；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(trityloxymethyl)oxan-2-yl]oxy-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 50705-44-7；108811-30-9
• 化学式: C₅₀H₅₀O₁₁
• 分子量: 826.94
• InChiKey: BJTFEBJIZYRLIR-BGSAPFNFSA-N

物化性质

• 熔点：
  191-193 °C
• 沸点：
  927.8±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  61
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  168
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-O-(triphenylmethyl)-α-D-glucopyranosyl-6'-O-(triphenylmethyl)-α-D-glucopyranoside 在 吡啶 、 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2,3,4,2',3',4'-hexa-O-acetyl-α,α-trehalose
  参考文献：
  名称：

  Synthesis of macrocycles on the basis of diterpenoid isosteviol and trehalose

  摘要：

  Macrocyclic glycoterpenoids containing trehalose and isosteviol fragments have been synthesized. Selective screening has revealed compounds exhibiting antitubercular activity against H37RV, M. Avium and M. Terrae at a level comparable to the known antitubercular drugs isoniazid, ofloxacin, and pyrazinamide.

  DOI：

  10.1134/s1070428015100231
• 作为产物：
  描述：

  2,3,4,2',3',4'-hexa-O-acetyl-6,6'-di-O-trityl-α,α-trehalose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以75%的产率得到6-O-(triphenylmethyl)-α-D-glucopyranosyl-6'-O-(triphenylmethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  An improved synthesis of (2,3,4-tri-O-acetyl-α-d-glucopyranosyl)uronic acid (2,3,4-tri-O-acetyl-α-d-glucopyranosid)uronic acid

  摘要：

  DOI：

  10.1016/s0008-6215(00)85440-3

文献信息

• Synthesis of the First Macrocyclic Glycoterpenoid Based on Trehalose and the Diterpenoid Isosteviol
  作者：B. F. Garifullin、R. R. Sharipova、I. Yu. Strobykina、O. V. Andreeva、V. E. Kataev

  DOI：10.1007/s10600-015-1440-3

  日期：2015.9

  A macrocyclic glycoterpenoid containing the diterpenoid dihydroisosteviol (16-hydroxy-ent-beyeran-19- oic acid) and α,α′-trehalose linked by an ester spacer was synthesized.

  合成了一种宏环糖萜类化合物，该化合物包含二萜类化合物二氢异斯特维醇（16-羟基-ent-贝亚酸）和由酯间隔连接的α,α'-海藻糖。
• Synthesis of Per- and Poly-Substituted Trehalose Derivatives: Studies of Properties Relevant to Their Use as Excipients for Controlled Drug Release
  作者：Thomas C. Baddeley、James L. Wardell

  DOI：10.1080/07328300902887672

  日期：2009.5.22

  substituents, included 6,6′-N,N′ -diamido-6,6′ -dideoxy-α,α -trehalose derivatives, 6,6′ -bis(1,2,3,4-tetra-O-acetyl-β -D-glucopyranuronyl)-α, α -trehalose derivatives, 2,2′,3,3′ -tetra-O-acetyl-6,6′ -bis-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′ -di-O-acyl-α,α-trehalose, 2, 2′, 3, 3′ -tetra-O-acetyl-6-(1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronyl)-4,4′,6′ -tri-O-acyl-α,α-trehalose, and 2,2′,3,3′,4

  已经制备了具有海藻糖核心的全取代和多取代的寡糖衍生物，并评估了它们在控释制剂中用作赋形剂的潜力。通常具有酰基和酰胺基取代基的合成化合物包括6,6'- N，N'-二叠氮基-6,6'-二脱氧-α，α-海藻糖衍生物，6,6'-双（1,2,3） ，4-四-O-乙酰基-β-D-吡喃葡萄糖醛酸基）-α，α-海藻糖衍生物，2,2'，3,3'-四-O-乙酰基-6,6'-双-（1,2 ，3,4-四-O-乙酰基-β-D-吡喃葡萄糖醛酸）-4,4'-二-O-酰基-α，α-海藻糖，2，2'，3，3'-四-O-乙酰基-6-（1,2,3,4-四-O乙酰基β-d-glucopyranuronyl）-4,4'，6' -三ö酰基-α，α -海藻糖，和2,2'，3,3'，4,4'-hexa- ö -乙酰基-6,6'-双-（1,2,3,4-四-O-乙酰基-6- O-琥珀酰基-β-D-吡喃葡萄糖醛酸基）-α，α-海藻糖。用NMR
• The natural product brartemicin is a high affinity ligand for the carbohydrate-recognition domain of the macrophage receptor mincle
  作者：Kristian M. Jacobsen、Ulrik B. Keiding、Lise L. Clement、Eva S. Schaffert、Neela D. S. Rambaruth、Mogens Johannsen、Kurt Drickamer、Thomas B. Poulsen

  DOI：10.1039/c4md00512k

  日期：——

  We demonstrate that the natural product brartemicin, a newly discovered inhibitor of cancer cell invasion, is a high-affinity ligand of the carbohydrate-recognition domain (CRD) of the C-type lectin mincle. Recent studies have revealed that mincle is a key macrophage receptor for the mycobacterial virulence factor trehalose dimycolate (TDM), which is a glycolipid component of the mycobacterial cell

  我们证明天然产物布雷替米星，一种新发现的癌细胞侵袭抑制剂，是C型凝集素微粒的糖类识别结构域（CRD）的高亲和力配体。最近的研究表明，mincle是分枝杆菌毒力因子海藻糖二甲藻酸酯（TDM）的关键巨噬细胞受体，TDM是分枝杆菌细胞壁的糖脂成分。然而，关于TDM结合和随后的信号转导以及潜在的共受体相互作用的主要不确定性。由于TDM的脂质性质，功能研究很困难，因此可溶性的微粒配体引起了极大的兴趣。因此，Brartemicin及其设计的类似物也可作为有用的分子探针，用于进一步研究mincle。
• Synthesis and structure–activity relationships studies of brartemicin analogs as anti-invasive agents
  作者：Yong-Li Jiang、Satoshi Miyanaga、Xiu-Zhen Han、Long-Qiang Tang、Yasuhiro Igarashi、Ikuo Saiki、Zhao-Peng Liu

  DOI：10.1038/ja.2013.37

  日期：2013.9

  Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to find more potent anti-invasive agents and study the structure–activity relationships, a series of 19 brartemicin analogs were prepared via two synthetic routes from α,α-D-trehalose and evaluated for their anti-invasive activities. Compound 4f, 6,6′-bis(2,3-dimethoxybenzoyl)-α,α-D-trehalose, was more potent than the natural brartemicin. It inhibited the invasion of murine colon 26-L5, colon carcinoma SW620, melanoma B16-BL6 and breast MDA-MB-231 cells with IC50 values of 0.15, 2.35, 4.12 and 2.61 μM, respectively. Analog 4p, 6,6′-bis(3,4-dimethoxycinnamoyl)-α,α-D-trehalose, was as potent as brartemicin against invasion of murine colon 26-L5 carcinoma cells in vitro. The structure–activity relationships of these novel trehalose-based compounds were summarized.

  Brartemicin是一种由Nonomuraea属放线菌产生的基于海藻糖的肿瘤细胞侵袭抑制剂。为了寻找更有效的抗侵袭剂并研究结构—活性关系，研究人员通过两条合成路线从α,α-D-海藻糖合成了一系列19种brartemicin类药物，并评估了它们的抗侵袭活性。化合物4f，6,6′-二(2,3-二甲氧基苯甲酰基)-α,α-D-海藻糖，比天然的brartemicin更为有效。它对小鼠结肠26-L5、结肠癌SW620、黑素瘤B16-BL6和乳腺MDA-MB-231细胞的侵袭抑制作用的IC50值分别为0.15、2.35、4.12和2.61μM。类药物4p，6,6′-二(3,4-二甲氧基肉桂酰基)-α,α-D-海藻糖，在体外对小鼠结肠26-L5癌细胞的侵袭抑制作用与brartemicin相当。这些新型基于海藻糖的化合物的结构—活性关系进行了总结。
• Synthesis and evaluation of trehalose-based compounds as anti-invasive agents
  作者：Yong-Li Jiang、Long-Qian Tang、Satoshi Miyanaga、Yasuhiro Igarashi、Ikuo Saiki、Zhao-Peng Liu

  DOI：10.1016/j.bmcl.2010.12.133

  日期：2011.2

  Brartemicin is a trehalose-based inhibitor of tumor cell invasion produced by the actinomycete of the genus Nonomuraea. In order to explore the preliminary structure–activity relationship and obtain more potent inhibitors, a series of brartemicin analogs were synthesized through the Mitsunobu coupling of the secondary hydroxyls benzyl protected α,α-d-trehalose with benzoic acid derivatives, followed by modification

  布雷替米星是一种基于海藻糖的诺诺氏菌属放线菌产生的肿瘤细胞侵袭抑制剂。为了探索初步的结构-活性关系并获得更多有效的抑制剂，通过将仲羟基苄基保护的α，α- d-海藻糖与苯甲酸衍生物进行Mitsunobu偶联，然后修饰功能性，合成了一系列的brartemicin类似物。组和脱保护。评价这些化合物在体外对鼠结肠26-L5癌细胞侵袭的抑制活性。在测试的合成类似物中，6,6'-双（2,3-二甲氧基苯甲酰基）-α，α- d-海藻糖（5e）被发现是最有效的抗侵袭剂，相对于母体天然产品brartemicin表现出2.6倍的改善，并且被认为是抗转移的有前途的先导分子。