allyl 4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside | 311349-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside
• 英文别名: 4,6-Di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside；[(2S,3R,4S,5S,6R)-5-acetyloxy-6-(acetyloxymethyl)-4-hydroxy-2-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 311349-74-3
• 化学式: C₂₀H₂₄O₉
• 分子量: 408.405
• InChiKey: AJUKSYYXVSUMHE-LYYGHALDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4,6-di-O-acetyl-2-O-benzoyl-3-O-chloroacetyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  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
• 作为产物：
  描述：

  allyl 2-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 硫酸 、 硫脲 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 19.67h， 生成 allyl 4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Yang; Kong, Synlett, 2000, # 10, p. 1423 - 1426

  摘要：

  DOI：