苄基 2,3,4-三-O-(苯基甲基)-6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷 | 78561-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 苄基 2,3,4-三-O-(苯基甲基)-6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷
• 英文名称: benzyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-mannopyranoside
• 英文别名: benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside；1,2,3,4-Tetra-O-benzyl-6-O-trityl-a-D-mannopyranose；(2S,3S,4S,5R,6R)-2,3,4,5-tetrakis(phenylmethoxy)-6-(trityloxymethyl)oxane
• CAS: 78561-22-5
• 化学式: C₅₃H₅₀O₆
• 分子量: 782.976
• InChiKey: GWEFKLSXFOMSCJ-MFYHPOFSSA-N

物化性质

• 沸点：
  829.9±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苄基 2,3,4-三-O-(苯基甲基)-6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷 在 potassium carbonate 、 对甲苯磺酸 、 2-碘酰基苯甲酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  一种抑制肿瘤细胞生长的药物组合物及其应用

  摘要：

  本发明公开了一种抑制肿瘤细胞生长的药物组合物，其有效成分包括M6CP‑OEt，该M6CP‑OEt的结构式为：本发明中的M6CP‑OEt能够在较低浓度下抑制包括骨肉瘤、肺癌和黑色素瘤在内的多种肿瘤细胞生长。

  公开号：

  CN109758465A
• 作为产物：
  描述：

  苯甲醇 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.33h， 生成 苄基 2,3,4-三-O-(苯基甲基)-6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷
  参考文献：
  名称：

  Glycosylated Platinum(IV) Complexes as Substrates for Glucose Transporters (GLUTs) and Organic Cation Transporters (OCTs) Exhibited Cancer Targeting and Human Serum Albumin Binding Properties for Drug Delivery

  摘要：

  Glycosylated platinum(IV) complexes were synthesized as substrates for GLUTs and OCTs for the first time, and the cytotoxicity and detailed mechanism were determined in vitro and in vivo. Galactoside Pt(IV), glucoside Pt(IV), and mannoside Pt(W) were highly cytotoxic and showed specific cancer-targeting properties in vitro and in vivo. Glycosylated platinum(W) complexes 5, 6, 7, and 8 (IC50 0.24-3.97 mu M) had better antitumor activity of nearly 166-fold higher than the positive controls cisplatin (1a), oxaliplatin (3a), and satraplatin (5a). The presence of a hexadecanoic chain allowed binding with human serum albumin (HSA) for drug delivery, which not only enhanced the stability of the inert platinum(IV) prodrugs but also decreased their reduction by reductants present in human whole blood. Their preferential accumulation in cancer cells compared to noncancerous cells (293T and 3T3 cells) suggested that they were potentially safe for clinical therapeutic use.

  DOI：

  10.1021/acs.jmedchem.7b00433

文献信息

• A nonself sugar mimic of the HIV glycan shield shows enhanced antigenicity
  作者：Katie J. Doores、Zara Fulton、Vu Hong、Mitul K. Patel、Christopher N. Scanlan、Mark R. Wormald、M. G. Finn、Dennis R. Burton、Ian A. Wilson、Benjamin G. Davis

  DOI：10.1073/pnas.1002717107

  日期：2010.10.5

  Antibody 2G12 uniquely neutralizes a broad range of HIV-1 isolates by binding the high-mannose glycans on the HIV-1 surface glycoprotein, gp120. Antigens that resemble these natural epitopes of 2G12 would be highly desirable components for an HIV-1 vaccine. However, host-produced (self)-carbohydrate motifs have been unsuccessful so far at eliciting 2G12-like antibodies that cross-react with gp120. Based on the surprising observation that 2G12 binds nonproteinaceous monosaccharide D-fructose with higher affinity than D-mannose, we show here that a designed set of nonself, synthetic monosaccharides are potent antigens. When introduced to the terminus of the D1 arm of protein glycans recognized by 2G12, their antigenicity is significantly enhanced. Logical variation of these unnatural sugars pinpointed key modifications, and the molecular basis of this increased antigenicity was elucidated using high-resolution crystallographic analyses. Virus-like particle protein conjugates containing such nonself glycans are bound more tightly by 2G12. As immunogens they elicit higher titers of antibodies than those immunogenic conjugates containing the self D1 glycan motif. These antibodies generated from nonself immunogens also cross-react with this self motif, which is found in the glycan shield, when it is presented in a range of different conjugates and glycans. However, these antibodies did not bind this glycan motif when present on gp120.

  抗体2G12通过结合HIV-1表面糖蛋白gp120上的高甘露糖基糖来独特地中和广泛范围的HIV-1分离株。类似于2G12这些天然抗原表位的抗原将是HIV-1疫苗中非常理想的组分。然而，迄今为止，宿主产生的（自身）糖基图案未能引发与gp120交叉反应的2G12类抗体。基于令人惊讶的观察结果，即2G12比D-甘露糖更具亲和力地结合非蛋白单糖D-果糖，我们在这里展示了一组设计的非自身合成单糖是强效抗原。当引入到2G12识别的蛋白糖基的D1臂末端时，它们的抗原性显著增强。对这些非天然糖的逻辑变化指出了关键的修饰，通过高分辨率晶体学分析阐明了这种增加的抗原性的分子基础。含有这种非自身糖的病毒样颗粒蛋白共轭物被2G12更牢固地结合。作为免疫原，它们引发的抗体滴度比包含自身D1糖基图案的免疫原共轭物更高。从非自身免疫原引发的这些抗体也与在多种共轭物和糖基中呈现的这种自身图案交叉反应，然而，当它出现在gp120上时，这些抗体不结合这种糖基图案。
• New syntheses of d- and l-glycero-d-manno-heptoses
  作者：Krzysztof Dziewiszek、Aleksander Zamojski

  DOI：10.1016/0008-6215(86)80013-1

  日期：1986.8

  Abstract Three methods for the synthesis of the title compounds starting from benzyl 2,3,4-tri-O-benzyl-α- d -manno-hexodialdo-1,5-pyranoside (7 have been elaborated. Conversion of 7 into the cyanohydrin followed by reduction to give the amine and then deamination gave a derivative of l -glycero- d -manno-heptose in low yield. Condensation of 7 with 2-methylfuran gave two stereoisomeric 6-C-(2-methyl-5-furyl)

  摘要合成了由苄基2,3,4-三-O-苄基-α-d-甘露六己醛-1,5-吡喃糖苷起始的三种标题化合物的合成方法（其中7种已被合成。7种转化为氰醇然后还原得到胺，然后脱氨基得到低产率的1-甘油-d-甘露庚糖衍生物，将7与2-甲基呋喃缩合得到两个立体异构体6-C-（2-甲基-5-呋喃基）。将主要的立体异构体进行臭氧处理，然后还原得到d-甘油-d-甘露庚糖衍生物，将7与烯丙氧基甲基镁氯化物缩合，可得到产率高且l-甘油d-甘油比率高的两种庚糖衍生物。这些衍生物的保护基比为3.2：1。脱保护得到的庚糖产率很高。
• Blood-group li-active oligosaccharides. Synthesis of O-β-D-galactopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→6)-D-mannose
  作者：Jocelyne Alais、Alain Veyrières

  DOI：10.1016/s0008-6215(00)80402-4

  日期：1981.6
• Synthesis of O-β-d-galactopyranosyl-(1→4)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6)-d-mannopyranose
  作者：Jan Arnarp、Jörgen Lönngren、H»kan Ottosson

  DOI：10.1016/s0008-6215(00)87154-2

  日期：1981.12