3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate | 483361-36-0

• 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)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate；allyl(-3)Glc2Ac4Ac6Ac(b1-3)[Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)]Glc2Ac4Ac(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,5-diacetyloxy-4-[(2S,3R,4S,5R,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-prop-2-enoxyoxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 483361-36-0
• 化学式: C₆₁H₆₂Cl₃NO₂₅
• 分子量: 1315.51
• InChiKey: LZUJBZLHDBUJND-YJMSAPKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  90
• 可旋转键数：
  34
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  325
• 氢给体数：
  1
• 氢受体数：
  26

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)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-methoxyphenyl 2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2.4-di-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-(1→6)-branched (1→3)-glucododecaose and -glucopentadecaose with alternate β- and α-bonds in the backbone

  摘要：

  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)]-alpha-D-Glcp-(1-->3)}(2-3)-beta-D-Glcp-(1-->3) -[beta-D-Glcp-(1-->6)]-beta-D-Glcp were synthesized as their methoxyphenyl glycosides in a concise way with a trisaccharide as the building block. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00354-9
• 作为产物：
  描述：

  2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 64.0h， 生成 3-O-allyl-2,4,6-tri-O-acetyl-β-D-glucopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)]-2,4-di-O-acetyl-α-D-glucopyranosyl trichloroacetimidate
  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 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
  作者：Xiangdong Mei、Linsen Heng、Mingkun Fu、Zhimin Li、Jun Ning

  DOI：10.1016/j.carres.2005.08.010

  日期：2005.10

  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.