methyl 2,3,6-tri-O-benzyl-4-O-[2'-O-benzoyl-4',6'-O-benzylidene-3'-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-[2'-O-benzoyl-4',6'-O-benzylidene-3'-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
• 英文别名: [(4aR,6S,7R,8S,8aS)-6-[(2R,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-2-phenyl-8-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] benzoate
• 化学式: C₈₂H₈₄O₁₇
• 分子量: 1341.56
• InChiKey: ZMVRKLOTSLEESF-CFHTVONPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  99
• 可旋转键数：
  32
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-[2'-O-benzoyl-4',6'-O-benzylidene-3'-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (4aR,6S,7R,8R,8aS)-6-((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-((2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues

  摘要：

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.058
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 六氢-1-(苯基硫代)-2H-氮杂卓-2-酮 、 三氟甲磺酸酐 、 camphor-10-sulfonic acid 、 hydrochloric acid diethyl ether 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-[2'-O-benzoyl-4',6'-O-benzylidene-3'-O-(2'',3'',4'',6''-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl]-β-D-glucopyranoside
  参考文献：
  名称：

  A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues

  摘要：

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.058

文献信息

• A new one-pot synthesis of Gb3 and isoGb3 trisaccharide analogues
  作者：Changning Wang、Qin Li、Haisheng Wang、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2006.09.058

  日期：2006.12

  Gb(3) and isoGb(3) are both biologically important oligosaccharides. A new efficient synthesis of Gb(3) and isoGb(3) trisaccharide analogues has been achieved by one-pot sequential glycosylation strategy starting from simple monosaccharide building blocks promoted by N-(phenylthio)-epsilon-caprolactam at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.