2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate | 171613-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate
• 英文别名: [(3S,4R,5S,6S)-4,5-dibenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 171613-12-0
• 化学式: C₂₈H₂₂Cl₃NO₈
• 分子量: 606.844
• InChiKey: CTJJXLYHZINRRA-MSZDEVHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate 、 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以82.3%的产率得到methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-[2,3,4-tri-O-benzoyl-β-L-xylopyranosyl-(1->2)][2,3,4-tri-O-benzoyl-β-L-xylopyranosyl-(1->4)]-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR Stenotrophomonas maltophilia SEROGROUP O18

  摘要：

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).

  DOI：

  10.1081/car-120003740
• 作为产物：
  描述：

  L-xylopyranose 在 吡啶 、 ammonium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate
  参考文献：
  名称：

  SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR Stenotrophomonas maltophilia SEROGROUP O18

  摘要：

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).

  DOI：

  10.1081/car-120003740

文献信息

• 10.1016/j.bmc.2024.117737
  作者：Sylla, Balla、Jost, Gilles、Lavoie, Serge、Legault, Jean、Gauthier, Charles、Pichette, André

  DOI：10.1016/j.bmc.2024.117737

  日期：——

  of ursane-type pentacyclic triterpenoids for pharmacological use is their poor aqueous solubility, which can impede their effectiveness as therapeutics agents. In this study, we present the facile synthesis of ursolic acid monodesmosides and uvaol bidesmosides, incorporating naturally occurring and water-soluble pentoses and deoxyhexose sugar moieties of opposite and -configurations at the C3 or C3/C28

  熊果酸和山楂醇是天然存在的三萜类化合物，具有广泛的药理活性，包括细胞毒性。然而，开发用于药理学用途的乌苏烷型五环三萜类化合物的主要挑战是它们的水溶性差，这可能妨碍它们作为治疗剂的有效性。在这项研究中，我们提出了熊果酸单链苷和乌苏醇双链苷的简便合成，在乌苏烷核心的C3或C3/C28位置掺入了天然存在的水溶性戊糖和脱氧己糖部分的相反和-构型。评估了二十种合成皂苷对肺癌（A549）和结直肠腺癌（DLD-1）细胞系的细胞毒性。值得注意的是，与它们的非细胞毒性母体三萜类化合物相比，所有双锁链乌苏醇皂苷均显示出细胞毒性。对于每个乌苏烷型皂苷系列，最活跃的化合物是 3--α 阿拉伯吡喃糖基熊果酸 () 和 3,28-二-α 吡喃鼠李糖基乌索醇 ()，显示出针对 A549 和 DLD-1 癌症的低微摩尔范围内的 IC 值线。
• Synthesis of an xylosylated rhamnose pentasaccharide, the repeating unit of the O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. begoniae GSPB 525
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00330-5

  日期：2002.3

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1 --> 3)-[beta-L-Xylp-(1 --> 2)-]-alpha-L-Rhap-(1 --> 3)-[beta-L-Xylp-(1 --> 4)]-L-Rhap, the repeating unit of the O-chain polysaccharide (OPS) of the lipo polysaccharides of Xanthomonas campestris pv. begoniae GSPB 525 was synthesized by a highly regio- and stereoselective way. Thus coupling of 1.2-O-ethylidene-beta-L-rhamnopyranose (1) with 2.3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (2) to give (1 --> 3)-linked disaccharide (3), subsequent benzoylation. deethylidenation, acetylation, 1-O-deacetylation, and trichloroacetimidation afforded the disaccharide donor 11. Condensation of 11 with 1 yielded 2.3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-2-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl-(1 --> 3)-1.2-O-ethylidene-beta-L-rhamnopyranose (12), and selective deacetylation of 12 yielded the trisaccharide diol acceptor 15. Coupling of 15 with 2.3.4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (16), followed by deprotection, gave the target pentasaccharide 19. (C) 2002 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR <i>Stenotrophomonas maltophilia</i> SEROGROUP O18
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1081/car-120003740

  日期：2002.5.31

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).