(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-4-(allyloxy)tetrahydro-2H-pyran-2,3,5-triyl tribenzoate | 908265-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-4-(allyloxy)tetrahydro-2H-pyran-2,3,5-triyl tribenzoate
• CAS: 908265-35-0
• 化学式: C₃₂H₃₀O₁₀
• 分子量: 574.584
• InChiKey: OKKPVTUIXHVNNV-PNKSDJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-4-(allyloxy)tetrahydro-2H-pyran-2,3,5-triyl tribenzoate 在 palladium dichloride 三氟甲磺酸三甲基硅酯 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 lauryl 6-O-acetyl-2,4-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-Glcp-(1→3)-[β-d-Glcp-(1→6)]-β-d-Glcp-(1→3)-β-d-Glcp-(1→6)-[β-d-Galp-(1→4)-β-d-Glcp-(1→3)]-β-d-GlcpOLauryl, an oligosaccharide with anti-tumor activity

  摘要：

  A concise and effective synthesis of lauryl heptasaccharide 17 was achieved from the key intermediates lauryl 2,3,4,6-tetra- O-benzoyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-benzoyi-beta-D-glucopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-beta-D-glucopyranoside (10) and isopropyl 2,4,6-tri-O-acetyl-3-O-allyl-beta-D-glucopyranosyl-(1-->3)-[2.3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-beta-D-glueopyranosyl-(1--> 3)-2,4,6-tri-O-acetyl-1-thio-beta-D-glucopyranoside (15). The key trisaccharide glycosyl acceptor 10 was constructed by coupling 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (3) with lauryl 6-O-acetyl-2,4-di-O-benzoyi-beta-D-glucopyranoside (9), followed by deacetylation. The thioglycoside donor 15 was obtained by condensation of 2,4,6-tri-O-acetyl-3-O-allyl-beta-D-glucopyranosyl-(1-->3)-[2,3,.4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyI trichloroacetimidate (11) with isopropyl 4,6-O-benzylidene-1-thio-beta-D-glucopyranoside (12), followed by debenzylidenation and acetylation. A bioassay of the inhibition of S-180 noumenal tumors showed that lauryl heptasaccharide 17 could be employed as a potential agent for cancer treatment. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.08.010
• 作为产物：
  描述：

  3-O-allyl-1,2,4-tri-O-benzoyl-6-O-triphenylmethyl-β-D-glucopyranose 在 吡啶 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-4-(allyloxy)tetrahydro-2H-pyran-2,3,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of β-d-Glcp-(1→3)-[β-d-Glcp-(1→6)]-β-d-Glcp-(1→3)-β-d-Glcp-(1→6)-[β-d-Galp-(1→4)-β-d-Glcp-(1→3)]-β-d-GlcpOLauryl, an oligosaccharide with anti-tumor activity

  摘要：

  A concise and effective synthesis of lauryl heptasaccharide 17 was achieved from the key intermediates lauryl 2,3,4,6-tetra- O-benzoyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-benzoyi-beta-D-glucopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-beta-D-glucopyranoside (10) and isopropyl 2,4,6-tri-O-acetyl-3-O-allyl-beta-D-glucopyranosyl-(1-->3)-[2.3,4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-beta-D-glueopyranosyl-(1--> 3)-2,4,6-tri-O-acetyl-1-thio-beta-D-glucopyranoside (15). The key trisaccharide glycosyl acceptor 10 was constructed by coupling 2,3,4,6-tetra-O-benzoyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (3) with lauryl 6-O-acetyl-2,4-di-O-benzoyi-beta-D-glucopyranoside (9), followed by deacetylation. The thioglycoside donor 15 was obtained by condensation of 2,4,6-tri-O-acetyl-3-O-allyl-beta-D-glucopyranosyl-(1-->3)-[2,3,.4,6-tetra-O-benzoyl-beta-D-glucopyranosyl-(1-->6)]-2,4-di-O-acetyl-alpha-D-glucopyranosyI trichloroacetimidate (11) with isopropyl 4,6-O-benzylidene-1-thio-beta-D-glucopyranoside (12), followed by debenzylidenation and acetylation. A bioassay of the inhibition of S-180 noumenal tumors showed that lauryl heptasaccharide 17 could be employed as a potential agent for cancer treatment. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.08.010