methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside | 151937-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
• 英文别名: methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucoside
• CAS: 151937-61-0
• 化学式: C₁₆H₂₄O₉
• 分子量: 360.361
• InChiKey: HRHCXSGRNHUCNX-IBEHDNSVSA-N

物化性质

• 沸点：
  428.0±45.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  106.59
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 methyl 3-O-allyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Corrie, John E. T., Journal of the Chemical Society. Perkin transactions I, 1993, # 18, p. 2161 - 2166

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4,6-Tetra-O-acetyl-3-O-allyl-β-D-glucopyranose 在 氨 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-glucose oligosaccharides from Phytophthora parasitica

  摘要：

  The glucohexaose, beta-D-Glcp-(1 --> 3)-[beta-D-Glcp-(1 --> 3)-beta-D-Glcp-(1 --> 3)-(3-D-Glcp-(1 --> 6)]-(3-D-Glcp-(1 --> 3)-o-Glcp, was synthesized as its allyl glycoside via 3+3 strategy. The trisaccharide donor, 2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranosyl-(1 --> 3)-2,4,6-tri-O-acetyl-alpha-D-glucopyranosyl trichloroacetimidate (11), was obtained by 3-selective coupling of isopropyl 4,6-O-benzylidene-1-thio-(3-D-glucopyranoside (2) with 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 3)-2-O-acetyl-4,6-O-benzylidene-alpha-D-glucopyranosyl trichloroacetimidate (6), followed by hydrolysis, acetylation, dethiolation, and trichloroacetimidation. Meanwhile, the trisaccharide acceptor, allyl 2,3,4,6-tetra-O-benzoyl-(3-D-glucopyranosyl-(1 --> 3)-2-O-acetyl(3-D-glucopyranosyl-(1 3)-4,6-di-O-acetyl-2-O-benzoyl-alpha-D-glucopyranoside (14), was prepared by coupling of allyl 4,6-di-Oacetyl-2-O-benzoyl-alpha-D-glucopyranoside (12) with 6, followed by debenzylidenation. Condensation of 14 with 11, followed by deacylation, gave the target hexaoside. A (3-(1 ->3)-linked tetrasaccharide 29 was also synthesized with methyl 2-O-benzoyl-4,6-0benzylidene-(3-D-glucopyranosyl-(1-> 3)-2,4,6-tri-O-acetyl-(3-D-glucopyranoside (25) as the acceptor and acylated (3-(1 3)-linked disaccharide 21 as the donor. 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.004