3-O-allyl-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate | 524037-13-6

• 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-benzoyl-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[allyl(-3)][Bz(-4)][Bz(-6)]Glc(a)-O-C(NH)CCl3；[(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-prop-2-enoxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 524037-13-6
• 化学式: C₃₂H₂₈Cl₃NO₉
• 分子量: 676.935
• InChiKey: KJZNKLZPQXXGDH-YFIKXWTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-allyl-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 氨 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.67h， 生成
  参考文献：
  名称：

  Synthesis of two heptasaccharide analogues of the lentinan repeating unit

  摘要：

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.003
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-4-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3,5-triol 在 吡啶 、 氨 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of two heptasaccharide analogues of the lentinan repeating unit

  摘要：

  beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-Benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.08.003

文献信息

• A KIND OF OLIGOSACCHARIDES, THEIR SULFATES AND DENDRIMERS, AND THE USES OF THESE COMPOUNDS
  申请人：Research Center for Eco-Environmental Sciences, Academia Sinica

  公开号：EP1405855A1

  公开（公告）日：2004-04-07

  This invention involves a type of oligosaccharides and its sulfate derivatives. The backbone of the oligosaccharides consists of 3 to 14 sugar residues, while the side chains contain 0 to 4 sugar residues. There is at least one 1→3α linkage in the backbone. This invention also involves the dendrimers composed of 2 to 3 oligosaccharides that are combined by polyhydroxyl compounds. These oligosaccharides, their sulfates and dendrimers have immune enhancing, antitumor, and antiviral activities. They can be used in immune enhancing, antitumor, and antiviral medicine compounds that would be used as therapeutic treatments.

  本发明涉及一种低聚糖及其硫酸盐衍生物。寡糖的主链由 3 至 14 个糖残基组成，侧链含有 0 至 4 个糖残基。主链中至少有一个 1→3α 连接。本发明还涉及由多羟基化合物结合的 2 至 3 个低聚糖组成的树枝状聚合物。这些寡糖、其硫酸盐和树枝状聚合物具有免疫增强、抗肿瘤和抗病毒活性。它们可用于免疫增强、抗肿瘤和抗病毒药物复合物中，作为治疗药物使用。
• Kind of oligosaccharides, their sulfates and dendrimers, and the uses of these compounds
  申请人：——

  公开号：US20040197289A1

  公开（公告）日：2004-10-07

  This invention involves a type of oligosaccharides and its sulfate derivatives. The backbone of the oligosaccharides consists of 3 to 14 sugar residues, while the side chains contain 0 to 4 sugar residues. There is at least one 1→3&agr; linkage in the backbone. This invention also involves the dendrimers composed of 2 to 3 oligosaccharides that are combined by polyhydroxyl compounds. These oligosaccharides, their sulfates and dendrimers have immune enhancing, antitumor, and antiviral activities. They can be used in immune enhancing, antitumor, and antiviral medicine compounds that would be used as therapeutic treatments.

  本发明涉及一种低聚糖及其硫酸盐衍生物。寡糖的主链由 3 至 14 个糖残基组成，侧链含有 0 至 4 个糖残基。骨架中至少有一个 1→3&agr; 连接。本发明还涉及由多羟基化合物结合的 2 至 3 个低聚糖组成的树枝状聚合物。这些寡糖、其硫酸盐和树枝状聚合物具有免疫增强、抗肿瘤和抗病毒活性。它们可用于免疫增强、抗肿瘤和抗病毒药物复合物中，作为治疗药物使用。
• Synthesis of an α-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6
  作者：Aixiao Li、Fanzuo Kong

  DOI：10.1016/j.carres.2004.07.026

  日期：2004.10

  A hexasaccharide, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-alpha-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->2)]-D-Glcp, the alpha-linked dimer of the trisaccharide repeating unit of the exopolysaccharide produced by Pediococcus damnosus 2.6, was synthesized as its methyl glycoside. Condensation of fully benzoylated alpha-D-glucopyranosyl trichloroacetimidate (1) with isopropyl 4,6-O-benzylid,ene-1-thio-beta-D-glucopyranoside (2) selectively furnished (1-->3)-linked disaccharide 3, and subsequent 2-O-acetylation, desulfation, and trichloroacetimidate formation afforded the disaccharide donor 6. Meanwhile, selective 3-O-coupling of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (8) with 3-O-allyl-2,4,6-tri-O-benzoyl-alpha-D-glucopyranosyl trichloroacetimidate (7), followed by coupling with 1 gave the trisaccharide 10. Removal of the benzylidene group of 10, benzoylation, and deallylation produced the trisaccharide acceptor 12. Condensation of 12 with 6 yielded a pentasaccharide mixture 13 with (3 and a isomers in a ratio of 2:1. Removal of the benzylidene group of 13, followed by benzoylation gave the pentasaccharide mixture 14. Selective 2"'-deacetylation of the isolated beta-linked 14 beta with MeCOCl/MeOH/CH2Cl2 did not give the expected pentasaccharide acceptor, and serious decomposition occurred, indicating a large steric hindrance at C-2"'. Alternatively, 2,3-di-O-glycosylation of allyl 4,6-O-benzylidene-beta-D-glucopyranoside (21) with 1 gave 22, then deallylation and trichloroacetimidate formation afforded the trisaccharide donor 24. Condensation of 12 with 24 furnished only the alpha-linked hexasaccharide 25, and its deprotection gave the free hexaoside 27. (C) 2004 Elsevier Ltd. All rights reserved.
• US7365191B2
  申请人：——

  公开号：US7365191B2

  公开（公告）日：2008-04-29