methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside | 76951-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-6)a-Man1Me2Ac3Ac4Ac；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 76951-67-2
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: PGJHXPDHJYQJOE-YYINZEDASA-N

物化性质

• 沸点：
  641.0±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 sodium methylate 作用下， 以96%的产率得到甲基 6-O-alpha-D-甘露糖基-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins

  摘要：

  For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose octaacetate (19) and O-alpha-D-mannopyranosyl-(1-->2)-O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose undecaacetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1-->3) (11) and (1-->6) (17) were chemically synthesized.

  DOI：

  10.1080/07328309808002903
• 作为产物：
  描述：

  Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins

  摘要：

  For the construction of N-glycoprotein glycan chains, valuable potential glycosyl donors, O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose octaacetate (19) and O-alpha-D-mannopyranosyl-(1-->2)-O-alpha-D-mannopyranosyl-(1-->2)-alpha-D-mannopyranose undecaacetate (20) were obtained in gram-scale by the acetylation and subsequent partial acetolysis of baker's yeast, without the isolation of mannan. The acetolytic products were investigated by matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. Octaacetates of mannobiose (1-->3) (11) and (1-->6) (17) were chemically synthesized.

  DOI：

  10.1080/07328309808002903

文献信息

• Stereoselective α-glycosidation using FeCl3 as a Lewis acid catalyst
  作者：Swapan K. Chatterjee、Peter Nuhn

  DOI：10.1039/a804533j

  日期：——

  A simplified procedure for the stereoselective α-glycosidation of peracetylated sugars, carrying a participating group at C2, with aliphatic alcohols in the presence of FeCl3 as a Lewis acid is described.

  描述了一种简化的程序，针对在C2位携带参与基团的全乙酰化糖与脂肪醇在存在氯化铁（FeCl3）作为路易斯酸的情况下进行立体选择性α-糖苷化。
• New Synthetic Methodology for Regio- and Stereoselective Synthesis of Oligosaccharides via Sugar Ortho Ester Intermediates
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1021/jo981135e

  日期：1998.8.1
• Synthesis of 1,2-trans-disaccharides via sugar thio-orthoesters
  作者：Leon V. Backinowsky、Yury E. Tsvetkov、Nikolay F. Balan、Narguiz E. Byramova、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(00)84672-8

  日期：1980.10
• Reactivity of 1,2-O-cyanoalkylidene sugar derivatives in trityl-cyanoalkylidene condensation
  作者：P. I. Kitov、Yu. E. Tsvetkov、L. V. Backinowsky、N. K. Kochetkov

  DOI：10.1007/bf00699947

  日期：1993.8

  The rate-determining step of trityl-cyanoalkylidene condensation is the interaction between the cyanoalkylidene derivative (CD) and the triphenylmethyl cation. The rate of the reaction follows first-order kinetics with respect to both CD and the catalyst (Tr+) and is independent of the nature and concentration of the trityl ether. Glycosylation rate constants have been determined for CD's of most common monosaccharides.
• Transglycosylation reactions with a crude culture filtrate from Thermoascusaurantiacus
  作者：Jörg Ortner、Martin Albert、Katherine Terler、Walter Steiner、Karl Dax

  DOI：10.1016/s0008-6215(00)00061-6

  日期：2000.8

  Some characteristics of regioselectivity and acceptor tolerance in transglycosylation reactions, catalysed by a crude culture filtrate from Thermoascus aurantiacus, were examined by employing methanol and monosaccharides as accepters. When beta-D-mannopyranosyl fluoride was employed as the donor, the anomeric configuration of the newly formed bond was found to depend on the structure of the acceptor used. (C) 2000 Elsevier Science Ltd. All rights reserved.