3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose | 483361-29-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose
• CAS: 483361-29-1
• 化学式: C₂₄H₃₆O₁₄
• 分子量: 548.541
• InChiKey: MWHLFNHTNKISDU-IWBMMQFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  174.74
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity

  摘要：

  A beta-(1 --> 6)-branched beta-(1 --> 3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(l --> 3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1 --> 3)linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-0-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1 --> 3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (I --> 6)-linked disaccharide 26 with 3-OH gave beta-(I --> 3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1 mg/kg substantially increased the inhibition of S 180 for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U-14 noumenal tumor in mice effectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00118-4
• 作为产物：
  描述：

  2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity

  摘要：

  A beta-(1 --> 6)-branched beta-(1 --> 3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its analogues 18, 20 and 33 containing an alpha-(l --> 3) linked bond were synthesized. It is interesting to find that coupling of a 3,6-branched acylated trisaccharide trichloroacetimidate donor 9 with 3,6-branched acceptors 13 and 16 with 3'-OH gave the alpha-(1 --> 3)linked hexasaccharides 17 and 19, respectively, in spite of the presence of C-2 ester capable of neighboring group participation. However, coupling of 9 with 4-methoxyphenyl 4,6-0-benzylidene-beta-D-glucopyranoside (27) selectively gave beta-(1 --> 3)-linked tetrasaccharide 28. Simple chemical transformation of the tetrasaccharide 28 gave acylated tetrasaccharide trichloroacetimidate 29. Coupling of 29 with lauryl (I --> 6)-linked disaccharide 26 with 3-OH gave beta-(I --> 3)-linked hexasaccharide 30 as the major product. Bioassay showed that in combination with the chemotherapeutic agent cyclophospamide (CPA), the hexaose 18 at a dose of 0.5-1 mg/kg substantially increased the inhibition of S 180 for CPA, but decreased the toxicity caused by CPA. Some of these oligosaccharides also inhibited U-14 noumenal tumor in mice effectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00118-4

文献信息

• Synthesis of Analogues of (1 → 6)‐Branched (1 → 3)‐Glucohexaose
  作者：Wei Zhao、Fanzuo Kong

  DOI：10.1081/car-200045260

  日期：2004.1

  beta-D-Galp-(1-->3)-[beta-D-Galp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 16 and beta-D-Galp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[alpha-D-Manp-(1-->6)-]D-Glcp 18 were synthesized as the analogues of the immunomodulator beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)-]alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)-]D-Glcp through coupling of trisaccharide donors 8 and 13 with trisaccharide acceptor 14 followed by deprotection, respectively.