allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside | 640722-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-3)Glc2Ac(b1-3)[Bz(-2)]Glc4Ac6Ac(a)-O-allyl；[(2R,3R,4S,5R,6S)-6-[(2S,3R,4S,5R,6R)-3-acetyloxy-2-[(2R,3R,4S,5R,6S)-3-acetyloxy-2-(acetyloxymethyl)-5-benzoyloxy-6-prop-2-enoxyoxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 640722-53-8
• 化学式: C₆₂H₆₂O₂₄
• 分子量: 1191.16
• InChiKey: SAVYYJKIPVJNLY-QHHLOBSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  86
• 可旋转键数：
  31
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  306
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-glucopyranoside 、 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-2,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到
  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：

  2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-acetyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-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