Xyl(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me | 1053645-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Xyl(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me
• 英文别名: (2S,3R,4S,5R)-2-[(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]oxyoxane-3,4,5-triol
• CAS: 1053645-96-7
• 化学式: C₆₀H₆₈O₁₅
• 分子量: 1029.19
• InChiKey: NPROTMARYJWZTB-ZXOPZENJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  75
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  171
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Xyl(b1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Glc1Me 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 methyl 2-O-(β-D-xylopyranosyl)-4-O-(β-D-mannopyranosyl)-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
• 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 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.5h， 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

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%.