2,3,4,6-tetra-O-acetyl-α-D-mannopyranose-(1-3)-methyl 2,4,6-tri-O-acetyl-α-D-mannopyranoside | 71978-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose-(1-3)-methyl 2,4,6-tri-O-acetyl-α-D-mannopyranoside
• 英文别名: Man2Ac3Ac4Ac6Ac(a1-3)a-Man1Me2Ac4Ac6Ac；[(2R,3R,4S,5S,6S)-3,5-diacetyloxy-6-methoxy-4-[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 71978-79-5
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: UHSQXNOZAXQAJT-JYNSOJRUSA-N

物化性质

• 沸点：
  649.8±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：

  2,3,4,6-tetra-O-acetyl-α-D-mannopyranose-(1-3)-methyl 2,4,6-tri-O-acetyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到甲基 3-O-alpha-D-甘露糖基-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  甲基3-O-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷和相关二糖的合成。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90315-x
• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-2,3-O-isopropylidene-α-D-mannopyranoside 在 4 A molecular sieve 、 水 、 氰化汞 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 、 mercury dibromide 作用下， 以 乙腈 、 苯 为溶剂， 反应 2.25h， 生成 2,3,4,6-tetra-O-acetyl-α-D-mannopyranose-(1-3)-methyl 2,4,6-tri-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  甲基3-O-α-D-甘露吡喃糖基-α-D-甘露吡喃糖苷和相关二糖的合成。

  摘要：

  DOI：

  10.1016/s0008-6215(00)90315-x

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。
• Anomalous Zemplén deacylation reactions of α- and β-d-mannopyranoside derivatives
  作者：Károly Ágoston、András Dobó、János Rákó、János Kerékgyártó、Zoltán Szurmai

  DOI：10.1016/s0008-6215(00)00283-4

  日期：2001.1

  Reaction of mono-, di-, and trisaccharide derivatives of methyl beta -D- and octyl beta -D-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplen conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds, in which the O-acyl groups were retained at isolated sites. In the case of one disaccharide, all the benzoyl groups remained intact at the reducing end, while all the acetyl functions were removable from the nonreducing end. In another case, both isolated ester groups at positions 2 and 4 were retained at the reducing end. The isolated 2-O-acyl groups on methyl alpha -D-mannopyranoside compounds were more labile than on the corresponding beta -mannosides under the same conditions. The mechanism of the reaction may be different for ester groups at isolated or non-isolated positions. In the latter case, acyl migration may take place and carry acyl groups into a less hindered position. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.
• Solid phase peptide templated glycosidic bond formation
  作者：Richard J. Tennant-Eyles、Benjamin G. Davis、Antony J. Fairbanks

  DOI：10.1016/s0957-4166(03)00118-6

  日期：2003.5

  Glycosylation reactions performed between a glycosyl donor and acceptor covalently linked to a peptide template both in the solution and solid phase give similar yields and product distributions. The adoption of a solid phase approach opens the way for the synthesis of libraries of peptide templates in an attempt to screen for particular peptide sequences that effect complete regio-and stereochemical control during glycosidic bond formation, whilst the use of second generation donors allows the possibility of an iterative approach. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and Semisynthesis of Some Structural Elements of Oligo-Mannose Type N-Glycoproteins
  作者：Zoltán Szurmai、Lóránt Jánossy、Zoltán Szilágyi、Károly Vékey

  DOI：10.1080/07328309808002903

  日期：1998.4

  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.