methyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 158819-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)]Xyl(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me；[(3R,4S,5R,6S)-4,5-dibenzoyloxy-6-[(2S,3S,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-3-yl] benzoate
• CAS: 158819-00-2
• 化学式: C₈₁H₈₀O₁₈
• 分子量: 1341.52
• InChiKey: QRNXNZHDKKEQHR-FMBHPVFGSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  99
• 可旋转键数：
  34
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 Xyl(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me
  参考文献：
  名称：

  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

  摘要：

  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%.

  DOI：

  10.1021/jo00101a036
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 silver aluminosilicate catalyst sodium tetrahydroborate 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.5h， 生成 methyl 2-O-(2,3,4-tri-O-benzoyl-β-D-xylopyranosyl)-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  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

  摘要：

  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%.

  DOI：

  10.1021/jo00101a036

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%.