phenyl-2,3,4-tri-O-methyl-α-L-rhamnopyranoside | 121820-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl-2,3,4-tri-O-methyl-α-L-rhamnopyranoside
• 英文别名: (2S,3S,4R,5R,6S)-3,4,5-trimethoxy-2-methyl-6-phenoxyoxane
• CAS: 121820-66-4
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: GSMOQRFVRNGZGK-MQFWEAQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tri-O-methyl-L-rhamnosyl fluoride 、 苯酚 在 二氯二茂铪 、 4 A molecular sieve 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以81%的产率得到phenyl-2,3,4-tri-O-methyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  RapidO-Glycosidation of Phenols with Glycosyl Fluoride by Using the Combinational Activator, Cp₂HfCl₂–AgClO₄

  摘要：

  描述了一种新的、有效的苯酚 O-糖苷化方法。 Cp2HfCl2–AgClO4 是糖基氟与苯酚在 4A 分子筛存在下的偶联反应的高效促进剂，该反应在低温下快速进行，高产率地生成 O-芳基糖苷。

  DOI：

  10.1246/cl.1989.437

文献信息

• Selective demethylation of <i>O</i>-aryl glycosides by iridium-catalyzed hydrosilylation
  作者：Caleb A. H. Jones、Nathan D. Schley

  DOI：10.1039/d1cc00496d

  日期：——

  The cleavage of alkyl ethers by hydrosilylation is a powerful synthetic tool for the generation of silyl ethers. Previous attempts to apply this transformation to carbohydrate derivatives have been constrained by poor selectivity and preferential reduction of the anomeric position. O-Aryl glycosides are found to be stable under iridium- and borane-catalyzed hydrosilylation conditions, allowing for

  通过氢化硅烷化裂解烷基醚是生成甲硅烷基醚的有力合成工具。以前将这种转化应用于碳水化合物衍生物的尝试受到选择性差和异头位置优先减少的限制。发现O-芳基糖苷在铱和硼烷催化的氢化硅烷化条件下是稳定的，允许在不损失异头官能团的情况下进行烷基醚裂解。阳离子双（膦）铱络合物催化各种 2,3,4-三-O-甲基吡喃糖的选择性 3-去甲基化，为 3-羟基或 3-乙酰基 2,4-二-O提供独特的方法-甲基吡喃糖。
• MATSUMOTO, TAKASHI;KATSUKI, MIYOKO;SUZUKI, KEISUKE, CHEM. LETT.,(1989) N, C. 437-440
  作者：MATSUMOTO, TAKASHI、KATSUKI, MIYOKO、SUZUKI, KEISUKE

  DOI：——

  日期：——
• DERIVATES OF AVERMECTIN,AVERMECTIN MONOSACCHARIDE AND AVERMECTIN AGLYCONE
  申请人：Syngenta Participations AG

  公开号：EP1789430A2

  公开（公告）日：2007-05-30
• [EN] DERIVATIVES OF AVERMECTIN, AVERMECTIN MONOSACCHARIDE AND AVERMECTIN AGLYCONE<br/>[FR] DERIVES DE L'AVERMECTINE, DE MONOSACCHARIDE DE L'AVERMECTINE, ET D'AGLYCONE DE L'AVERMECTINE
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2006024405A2

  公开（公告）日：2006-03-09

  A compound of the formula (I) wherein the bond between carbon atoms 22 and 23 indicated with a broken line is a single or double bond, n is 0, 1 or 2, R1 represents, for instance, a C1-C12alkyl group, R2 represents, for instance, R15 group, R3 represents, for instance, R2 group, R4 represents, for instance, a chemical constituent, R5 represents, for instance, hydrogen, and R6 represents, for instance, R16 group; wherein R15 represents, for instance, unsubstituted or mono- to pentasubstituted C1-C6alkyl group, and R16 represent, for instance, hydrogen, or R15; and if appropriate, an E/Z isomer and/or diastereoisomer and/or tautomer of the compound of formula (I), in each case in free form or in salt form. Such compounds have been found to have pesticidal properties.
• Rapid<i>O</i>-Glycosidation of Phenols with Glycosyl Fluoride by Using the Combinational Activator, Cp₂HfCl₂–AgClO₄
  作者：Takashi Matsumoto、Miyoko Katsuki、Keisuke Suzuki

  DOI：10.1246/cl.1989.437

  日期：1989.3

  A new and efficient method for O-glycosidation of phenols is described. Cp2HfCl2–AgClO4 is a highly effective promoter for the coupling reaction between glycosyl fluoride and phenol in the presence of molecular sieves 4A, which proceeds rapidly at low temperature to give O-aryl glycoside in high yields.

  描述了一种新的、有效的苯酚 O-糖苷化方法。 Cp2HfCl2–AgClO4 是糖基氟与苯酚在 4A 分子筛存在下的偶联反应的高效促进剂，该反应在低温下快速进行，高产率地生成 O-芳基糖苷。