(2S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-dihydro-pyran-3,3-diol | 98925-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-dihydro-pyran-3,3-diol
• CAS: 98925-55-4
• 化学式: C₅₅H₆₀O₁₂
• 分子量: 913.074
• InChiKey: NQSLAQUKQFLYRE-OYWVFDQOSA-N

物化性质

• 沸点：
  948.6±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.92
• 重原子数：
  67.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  132.76
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-dihydro-pyran-3,3-diol 在 palladium on activated charcoal lithium aluminium tetrahydride 、 盐酸羟胺 、 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4-O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  A new approach to the synthesis of β-glycosidically linked oligosaccharides containing 2-acetamido-2-deoxy-d-mannose residues

  摘要：

  DOI：

  10.1016/0008-6215(85)90030-8
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 乙酸酐 、 二甲基亚砜 作用下， 以77%的产率得到(2S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-dihydro-pyran-3,3-diol
  参考文献：
  名称：

  A new approach to the synthesis of β-glycosidically linked oligosaccharides containing 2-acetamido-2-deoxy-d-mannose residues

  摘要：

  DOI：

  10.1016/0008-6215(85)90030-8

文献信息

• Practical Synthesis of .beta.-D-Xyl-(1.fwdarw.2)-.beta.-D-Man-(1.fwdarw.4)-.alpha.-D-Glc-OMe, a Trisaccharide Component of the Hyriopsis schlegelii Glycosphingolipid
  作者：Frieder W. Lichtenthaler、Thomas Schneider-Adams、Stefan Immel

  DOI：10.1021/jo00101a036

  日期：1994.11

  By employing the readily accessible (preceding paper in this issue) 3,4,6-tri-O-benzyl-alpha-D-arabino-hexosyl bromide (1) as an indirect, beta-specific mannosyl donor, a practical three-step synthesis was elaborated for methyl xylosyl-beta(1-->2)-mannosyl-beta(1-->4)-glucoside (11), a trisaccharide component of Hyriopsis schlegelii ceramide oligosaccharides. Key steps were the silver aluminosilicate-induced, beta-specific glycosidation of 1 with methyl 2,3,6-tri-O-benzyl-alpha-D-glucoside and the silver triflate-promoted beta-xylosylation with 2,3,4-tri-O-benzoyl-alpha-D-xylosyl bromide. The overall yield amounted to a satisfactory 47%.