4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose | 83866-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose
• 英文别名: 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl trichloroacetimidate；[(3aR,4S,6S,7S,7aR)-2,2,6-trimethyl-4-(2,2,2-trichloroethanimidoyl)oxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] acetate
• CAS: 83866-17-5
• 化学式: C₁₃H₁₈Cl₃NO₆
• 分子量: 390.648
• InChiKey: HPNVNDZPRNBITH-GWYYCADCSA-N

物化性质

• 沸点：
  379.2±52.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 dodecanyl 4-O-acetyl-2,3-O-isopropylidene-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1->3)-4-O-acetyl-2-O-levulinoyl-α-L-rhamnopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
  参考文献：
  名称：

  分离自油菜（Cleistopholis patens）和油酸油菜（Cleistopholis glauca）的部分部分乙酰化的十二烷酰基四十二烷衍生物cleistetroside-2的全合成。

  摘要：

  首次实现了部分乙酰化的十二烷基四鼠李糖苷衍生物cleistetroside-2的总合成，该衍生物是从Cleistopholis patens和Cleistopholis glauca中分离出来的，并且对革兰氏阳性细菌显示出显着的体外抗菌活性。

  DOI：

  10.1016/j.carres.2007.03.014
• 作为产物：
  描述：

  1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 14.0h， 生成 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose
  参考文献：
  名称：

  Facile synthesis of cleistetroside-2, a partially acetylated oligorhamnoside from Cleistopholis glauca and patens

  摘要：

  A tetrasaccharide, dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 3)-4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-alpha-L-rhamnopyranoside (cleistetroside-2), was synthesized via '2+2' convergent strategy. Sequential regioselective 3-O-glycosylation of isopropyl 1-thio-alpha-L-rhamnopyranoside (4) with 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl trichloroacetimidate (8), and isopropyl 4-O-acetyl-2,3-O-isopropylidene-alpha-L-rhamnopyranosyl-(1 -> 3)-2,4-di-O-acetyl-alpha-L-1-thio-rh amnopyranoside (10) with dodecanyl 4-O-acetyl-alpha-L-rhamnopyranosyl-(1 -> 4)-2,3-O-isopropylidene-alpha-L-rharnnopyranoside (12), greatly facilitate the target availability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.05.019

文献信息

• Design, Synthesis and Structure-Activity Relationship of Novel Aphicidal Mezzettiaside-Type Oligorhamnosides and Their Analogues
  作者：Hui Zhao、Zhuwen Wei、Zhiyan Jiang、Sumei Li、Yixian Liao、Yiming Guo、Yongmei Tang、Weihao Chen、Guohua Zhong、Gaopeng Song

  DOI：10.3390/molecules23010041

  日期：——

  environmentally friendly insect control in the agricultural industry. In order to discover novel eco-friendly pesticides, a series of partially acetylated oligorhamnoses mezzettiasides, 2-8, and their analogues, 9-14, with biosurfactant characteristics were designed and synthesized, some of which exhibited comparable to or even stronger aphicidal activity than pymetrozine. Preliminary SAR studies demonstrated

  低聚糖已被用于农业工业中的环境友好的昆虫防治。为了发现新型的生态友好型农药，设计并合成了具有生物表面活性剂特性的一系列部分乙酰化的低聚羊驼毛2-8号及其类似物9-14，其中一些具有比甚至更强的杀蚜活性。吡me嗪 SAR的初步研究表明，美甲etti类似物的杀蚜活性在很大程度上取决于其结构，包括糖长和糖上的替代物。其中，鼠李糖脂9表现出最强的杀菌活性，LC50为0.019 mmol / L，表明该生物表面活性剂9可能具有用作环境友好型农业农药的潜力。
• Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions
  作者：Nora Katharina Korber、Christian Marcus Pedersen

  DOI：10.1016/j.carres.2021.108497

  日期：2022.1

  Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-l-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-α-l-rhamnopyranose in combination with the two alcohols 1-adamantanol and l-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated

  用两个糖基供体 4 - O-乙酰基-2,3- O-异亚丙基-1- O-三氯乙亚氨基-α- 1-吡喃鼠李糖和 2,3,4-三-O-苄基-1- O进行糖基化-三氯-乙酰亚氨基-α-L-吡喃鼠李糖与两种醇1-金刚烷醇和L-薄荷醇组合作为模型糖基受体。作为催化剂，五种锂盐LiNTf 2、LiI、LiClO 4、LiPF 6和 LiOTf 进行了调查。我们证明了锂和各自的抗衡离子都在室温下激活三氯乙酰亚胺酯糖基供体中发挥作用。在这些非常温和的条件下，糖基化缓慢并在两到八天内完成。取决于抗衡离子，反应的速率和产率不同；然而，所有研究的锂盐的选择性都不足。
• Synthesis and antibacterial evaluation of a series of oligorhamnoside derivatives
  作者：Ning Ding、Zaihong Zhang、Wei Zhang、Yuexing Chun、Peng Wang、Huimin Qi、Shan Wang、Yingxia Li

  DOI：10.1016/j.carres.2011.07.028

  日期：2011.10

  A series of novel oligorhamnoside derivatives (1-10) and naturally occurring cleistrioside-5 were synthesized and evaluated for their in vitro antibacterial activities. Among them, dirhamnoside derivative 7 and cleistrioside-5 displayed similar antibacterial profiles and exhibited moderate to good inhibitory activities on bacterial growth against a panel of Gram-positive bacteria (MICs <= 4-32 mu g/mL). The results revealed that these two compounds showed selectivity towards bacterial species strictly, without being affected by the antibiotic-resistant/susceptible properties of one species, which suggested that they might have the potential to avoid antibiotic cross-resistance. In addition, the preliminary SARs of this type of oligorhamnoside derivatives on the antibacterial activities were determined. (C) 2011 Elsevier Ltd. All rights reserved.
• Retention of the anomeric configuration in the imidate procedure: synthesis of disaccharides containing α-l-rhamnopyranosyl and α-d-mannopyranosyl groups
  作者：Péter Fügedi、András Lipták、Pál Nánási、András Neszmélyi

  DOI：10.1016/s0008-6215(00)80788-0

  日期：1982.9