甲基2,3,4,6-四-O-苄基-D-吡喃甘露糖苷 | 83462-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基2,3,4,6-四-O-苄基-D-吡喃甘露糖苷
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-D-mannopyranoside
• 英文别名: tetrabenzylmethyl-D-mannopyranoside；methyl-2,3,4,6-tetra-O-benzylmannoside；Methyl-2,3,4,6-tetra-O-benzyl-mannopyranoside；(3S,4S,5R,6R)-2-methoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 83462-67-3
• 化学式: C₃₅H₃₈O₆
• 分子量: 554.683
• InChiKey: IXEBJCKOMVGYKP-DLCPRKGNSA-N

物化性质

• 沸点：
  656.9±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  甲基2,3,4,6-四-O-苄基-D-吡喃甘露糖苷 在 硫酸 、 sodium hydride 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 9.17h， 生成 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Cardiac glycosides. 7. Sugar stereochemistry and cardiac glycoside activity

  摘要：

  Digitoxigenin alpha-L-, beta-L-, alpha-D-, and beta-D-glucosides; alpha-L-, beta-L-, alpha-D-, and beta-D-mannosides; and alpha-L- and beta-L-rhamnosides were stereoselectively synthesized from the corresponding sugar tetrabenzyl trichloroacetimidates. The Na+,K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those of digitoxigenin, digitoxigenin 6'-hydroxy-beta-D-digitoxoside, digitoxigenin beta-D-galactoside, and digitoxigenin beta-D-digitoxoside. The observed activities reveal that a given sugar substituent may have a role in binding of some glycoside stereoisomers, but not others. With alpha-L- and possibly beta-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the Na+,K+-ATPase receptor. Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the alpha-L isomer. However, with the beta-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains. With beta-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly. With these beta-D-glycosides, an equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

  DOI：

  10.1021/jm00160a025
• 作为产物：
  描述：

  甘露糖 在 氯化亚砜 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 甲基2,3,4,6-四-O-苄基-D-吡喃甘露糖苷
  参考文献：
  名称：

  Enhanced Spacer Length between Mannose Mimicking Shikimoyl and Quinoyl Headgroups and Hydrophobic Region of Cationic Amphiphile Increases Efficiency of Dendritic Cell Based DNA Vaccination: A Structure–Activity Investigation

  摘要：

  In the field of dendritic cell based genetic immunization, previously we showed that liposomes of cationic amphiphiles containing mannose-mimicking shikimoyl headgroup are promising DNA vaccine carriers for dendritic cell (DC) transfection. The present structure activity study reports on the influence of spacer length (between mannose-mimicking headgroups and quaternary nitrogen centers) in modulating the DC-transfection efficiencies. Further, we report on the anti melanoma immune response inducing properties of the promising cationic amphiphiles in syngeneic CS7BL/6J mice under prophylactic settings.

  DOI：

  10.1021/acs.jmedchem.6b01556

文献信息

• Stereospecific cyclization to form C-furanosides
  作者：Bing-Hui Yang、Ji-Qing Jiang、Kan Ma、Hou-Ming Wu

  DOI：10.1016/0040-4039(95)00413-7

  日期：1995.4

  A cyclization of benzyl ethers with Sn2 active site at γ-position to form C-furanoside was studied.

  研究了在γ位具有S n 2活性位的苄基醚的环化反应，形成C-呋喃糖苷。
• Novel compounds and methods
  申请人：PharmAxis Pty Ltd.

  公开号：US20030176363A1

  公开（公告）日：2003-09-18

  The present invention provides phosphotetrahydropyran compounds and the use thereof in treating diseases or conditions that are dependent on T-lymphocyte migration, as well as compositions containing said compounds.

  本发明提供了磷酸四氢吡喃化合物及其在治疗依赖于T淋巴细胞迁移的疾病或症状中的用途，以及含有该类化合物的组合物。
• Phospholipid-saccharide conjugates
  申请人：Genzyme Corporation

  公开号：US05354853A1

  公开（公告）日：1994-10-11

  Novel phospholipid-saccharide conjugates are produced by the reaction of a phospholipid derivative and an activated saccharide. The resulting conjugates can be used to make liposomes which are target-specific or resistant to degradation in vivo.

  新型磷脂酰类和糖醛酸盐结合物通过磷脂酰类衍生物和活性糖醛酸盐的反应制备而成。所得的结合物可用于制备靶向特异性或体内抗降解的脂质体。
• 2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors
  作者：Jinq-Chyi Lee、Guan-Rong Pan、Suvarn S. Kulkarni、Shun-Yuan Luo、Chun-Chen Liao、Shang-Cheng Hung

  DOI：10.1016/j.tetlet.2005.12.127

  日期：2006.3

  A high-yielding coupling of a new and stable type of glycosyl donors, namely 2-allyloxyphenyl glycoside, with a variety of alcohols via NIS/TfOH reagent combination as effective activators at room temperature is described here. (c) 2006 Elsevier Ltd. All rights reserved.
• NOVEL PHOSPHOLIPID-SACCHARIDE CONJUGATES
  申请人：GENZYME CORPORATION

  公开号：EP0688329B1

  公开（公告）日：2002-05-15