4-methoxyphenyl α-L-rhamnopyranoside | 18918-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl α-L-rhamnopyranoside
• 英文别名: p-methoxyphenyl α-L-rhamnopyranoside；4-Methoxyphenyl 6-deoxy-I+/--L-mannopyranoside；(2S,3R,4R,5R,6S)-2-(4-methoxyphenoxy)-6-methyloxane-3,4,5-triol
• CAS: 18918-36-0
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: QYXDZVRPDLEXIN-HPMQQCADSA-N

物化性质

• 沸点：
  457.1±45.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl α-L-rhamnopyranoside 在 吡啶 、 D(+)-10-樟脑磺酸 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.75h， 生成 4-methoxyphenyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the Trisaccharide Repeating Unit of the O‐Antigen Related to the EnterohemorrhagicEscherichia coliType O26:H

  摘要：

  L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H.

  DOI：

  10.1081/car-120020480
• 作为产物：
  描述：

  L-鼠李糖 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 4-methoxyphenyl α-L-rhamnopyranoside
  参考文献：
  名称：

  炭疽杆菌四糖抗原的全合成-炭疽疫苗候选物的创建。

  摘要：

  DOI：

  10.1002/anie.200502615

文献信息

• Catalytic Site-Selective Carbamoylation of Pyranosides
  作者：Jérôme Alsarraf、Lucas Petitpoisson、André Pichette

  DOI：10.1021/acs.orglett.1c02116

  日期：2021.8.6

  Carbamate-bearing carbohydrates contribute to the pharmacological properties of various natural glycosides. The catalytic site-selective carbamoylation of minimally protected pyranosides was achieved for the first time to bypass protection/deprotection sequences. 1-Carbamoylimidazoles were used as the carbamoylation reagents to circumvent the harmful and unstable phosgene and isocyanates. This borinic

  含氨基甲酸酯的碳水化合物有助于各种天然糖苷的药理特性。首次实现了最低限度保护的吡喃糖苷的催化位点选择性氨基甲酰化，以绕过保护/脱保护序列。1-氨基甲酰咪唑被用作氨基甲酰化试剂以规避有害且不稳定的光气和异氰酸酯。这种硼酸催化的转化使博来霉素和类似物的肿瘤细胞结合氨基甲酰甘露糖苷部分能够以 56% 至 89% 的产率获得。
• Indium Trichloride Mediated Cleavage of Acetonides in the Presence of Acid-Labile Functional Groups - Enhancing the Synthetic Utility of 1,3-Dioxolanyl-Substituted 1,2-Oxazines
  作者：Hans-Ulrich Reissig、Fabian Pfrengle、Vjekoslav Dekaris、Luise Schefzig、Reinhold Zimmer

  DOI：10.1055/s-0028-1083628

  日期：2008.12

  Indium trichloride in an acetonitrile-water mixture chemoselectively cleaved the isopropylidene acetals of various 1,3-dioxolanyl-substituted 1,2-oxazines as well as carbohydrate derivatives. Deprotection of acetonides can be achieved in substrates susceptible for acid-induced cyclizations. Most importantly, enol ether moieties are not attacked and the presence of glycosidic linkages or acid-sensitive protecting groups such as tert-butyldimethylsilyl, 2-(trimethylsilyl)ethyl, or tert-butoxycarbonyl is also tolerated.

  三氯化铟在乙腈-水混合物中能化学选择性地裂解各种 1,3- 二氧戊环取代的 1,2- 氧嗪的异亚丙基乙醛以及碳水化合物衍生物。在易受酸诱导环化作用影响的底物中，可以实现丙酮的脱保护。最重要的是，烯醇醚分子不会受到侵蚀，而且还能承受糖苷键或对酸敏感的保护基团（如叔丁基二甲基硅基、2-（三甲基硅基）乙基或叔丁氧基羰基）的存在。
• Synthesis of aryl α-<i>O-</i>L-rhamnopyranoside by two-step reaction in one pot
  作者：Nianping Liu、Xiangguang Tian、Zekun Ding、Yongda Zhou、Wan Zhang、Qingbing Wang、Yi Zhang、Yijun Gu、Jianbo Zhang

  DOI：10.1080/07328303.2017.1390578

  日期：2017.6.13

  approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The two-step one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed by means of the Hammett equation.

  图形摘要摘要使用鼠李糖吡喃糖基氯为主要中间体，通过两步一锅的相转移催化方法方便地合成了标题化合物。与公开的合成路线相比，两步一锅法更方便，更环保。此外，利用Hammett方程讨论了该碱催化的糖基化反应的结构-反应关系和合理的机理。
• Efficient synthesis of a 6-deoxytalose tetrasaccharide related to the antigenic O-polysaccharide produced by Aggregatibacter actinomycetemcomitans serotype c
  作者：Xiangyan Cai、Guanghui Zong、Yanjun Xu、Jianjun Zhang、Xiaomei Liang、Daoquan Wang

  DOI：10.1016/j.carres.2010.04.009

  日期：2010.6

  actinomycetemcomitans serotype c, has been accomplished through suitable protecting group manipulations and stereoselective glycosylation starting from commercially available L-rhamnose. The target oligosaccharide in the form of its p-methoxyphenyl glycoside is suitable for further glycoconjugate formation via selective cleavage of this group.

  精确合成6-脱氧-α-L-塔洛糖四糖，6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp-（1-> 2） -6-脱氧-α-L-Talp-（1-> 3）-6-脱氧-α-L-Talp，是来自血清型c的放线杆菌的OPS的二糖重复单元的二聚体，已经通过合适的方法完成。从可商购的L-鼠李糖开始的保护基操纵和立体选择性糖基化。对-甲氧基苯基糖苷形式的目标寡糖适合通过该基团的选择性切割进一步形成糖缀合物。
• Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum
  作者：Santanu Mandal、Balaram Mukhopadhyay

  DOI：10.1016/j.tet.2007.08.077

  日期：2007.11

  Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developed using H2SO4 immobilized on silica for activation of trichloroacetimidate donors, or in conjunction with N-iodosuccinimide for activation of a thioglycoside. A late stage TEMPO-mediated oxidation was performed for

  报道了从炭疽病菌中分离出的与皂苷有关的两种三糖的化学合成。使用固定在二氧化硅上的H 2 SO 4活化三氯乙酰亚氨酸酯供体，或与N-碘琥珀酰亚胺联用来活化硫糖苷，开发了立体选择性，高产糖基化策略。进行后期TEMPO介导的氧化，以形成所需的糖醛酸部分。