methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 51842-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• 英文别名: Methyl-2,3-di-O-benzyl-4,6-O-benzyliden-α-D-mannopyranosid；Methyl-2.3-di-O-benzyl-4.6-O-benzyliden-α-D-mannopyranosid；Methyl 2,3-DI-O-benzyl-4,6-O-benzylidene-A-D-mannopyranoside；(4aR,6S,7S,8S,8aR)-6-methoxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 51842-18-3
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: CVHUOBYFXKHVJR-RARZINSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 以94.7%的产率得到((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇
  参考文献：
  名称：

  Liptak, A.; Goendoer, A., Acta Chimica Hungarica, 1983, vol. 114, # 3-4, p. 309 - 322

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl endo-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  糖醛酸甲基醚的合成。三、甲基（甲基α-D-吡喃甘露糖苷）糖醛酸及其2-和4-0-甲基醚的合成

  摘要：

  甲基（α-D-吡喃甘露糖苷）糖醛酸甲酯及其2-和4-0-甲基醚的合成是通过三氧化铬氧化相应的α-D-吡喃甘露糖苷的O-苄基和O-亚苄基衍生物来实现的，用重氮甲烷酯化，然后通过催化氢解消除保护性苄基或亚苄基。

  DOI：

  10.1007/bf00575690

文献信息

• Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction
  作者：Jia-Lu Xue、Xiao-Peng He、Jin-Wei Yang、De-Tai Shi、Chao-Ying Cheng、Juan Xie、Guo-Rong Chen、Kaixian Chen

  DOI：10.1016/j.carres.2012.10.001

  日期：2012.12

  Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (similar to 70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media. (C) 2012 Elsevier Ltd. All rights reserved.
• Lysosomal-enzyme targeting: the phosphorylation of synthetic d-mannosyl saccharides by UDP-N-acetylglucosamine:lysosomal-enzyme N-acetylglucosaminephosphotransferase from rat-liver microsomes and fibroblasts
  作者：Ragupathy Madiyalakan、Manjit S. Chowdhary、Surjit S. Rana、Khushi L. Matta

  DOI：10.1016/s0008-6215(00)90298-2

  日期：1986.9

  Phosphorylation of the D-mannose residues of lysosomal enzymes is essential for the uptake and intracellular transport of these enzymes to lysosomes. The GlcNAc-P-transferase which is involved in the phosphorylation reaction seems to recognize a signal, probably a protein conformation, common to many lysosomal enzymes. To evaluate the role of the carbohydrate portion of the enzyme in these phosphorylation reactions, the acceptor specificity of GlcNAc-P-transferase from rat-liver microsomes and fibroblasts was examined with the aid of synthetic D-mannosyl disaccharides and derivatives that are closely related to the high-mannose type of oligosaccharides. Four methyl D-mannobiosides were synthesized, and their structures were established by 13C-n.m.r. spectroscopy. Of all the D-mannosyl saccharides tested, alpha-D-Man-(1----2)-alpha-D-Man-(1----OMe) was found to be the best acceptor, thereby suggesting that oligosaccharide structure may also have a role to play in recognition by this enzyme.
• Liptak, A.; Goendoer, A., Acta Chimica Hungarica, 1983, vol. 114, # 3-4, p. 309 - 322
  作者：Liptak, A.、Goendoer, A.

  DOI：——

  日期：——
• SHAH, RAJAN N.;BAPTISTA, JOSE;PERDOMO, GUILLERMO R.;CARVER, JEREMY P.;KRE+, J. CARBOHYDR. CHEM., 6,(1987) N 4, 645-660
  作者：SHAH, RAJAN N.、BAPTISTA, JOSE、PERDOMO, GUILLERMO R.、CARVER, JEREMY P.、KRE+

  DOI：——

  日期：——
• Partial benzylation of methyl 4,6-O-benzylidene-α-d-mannopyranoside
  作者：Yôtaro Kondo、Kazuhiko Noumi、Shigemi Kitagawa、Shigehiro Hirano

  DOI：10.1016/0008-6215(83)88391-8

  日期：1983.11