3-(C-lactosyl)-2-propanone | 1131343-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(C-lactosyl)-2-propanone
• CAS: 1131343-96-8
• 化学式: C₁₅H₂₆O₁₁
• 分子量: 382.365
• InChiKey: CZPVHXTZZCIQGE-LYUPDXEASA-N

物化性质

• 沸点：
  684.6±55.0 °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)：
  -4.37
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  186.37
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3-(C-lactosyl)-2-propanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以65%的产率得到(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-hydroxypropyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media

  摘要：

  The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane(TM)) was identified as the best activator of GAGs biosynthesis. Pro-Xylane(TM) was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.037
• 作为产物：
  描述：

  Lactose 、 乙酰丙酮 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 12.0h， 以79%的产率得到3-(C-lactosyl)-2-propanone
  参考文献：
  名称：

  Synthesis of Pro-XylaneTM: A new biologically active C-glycoside in aqueous media

  摘要：

  The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane(TM)) was identified as the best activator of GAGs biosynthesis. Pro-Xylane(TM) was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.037

文献信息

• C-GLYCOSIDE COMPOUNDS, AND METHOD FOR PREPARING C-GLYCOSIDE COMPOUNDS
  申请人：Benvegnu Thierry

  公开号：US20110245490A1

  公开（公告）日：2011-10-06

  The invention relates to C-glycose compounds of formula (I) where: S′ is a monosaccharide radical or a polysaccharide radical derived from a monosaccharide or polysaccharide S; R is a linear or branched alkyl radical; and Z is an ethylenyl CH═CR1(R2) or an acetylenyl C≡CR3 radical. The invention also relates to a method for preparing C-glycoside compounds of formula (III), characterised in that the method consists of a step of reacting a sugar (S), in an aqueous solvent or in the absence of a solvent and in the presence of an organic or mineral base (B), with a phosphonate of formula (II) according to the following reaction pattern: Formulas (II), (III).

  该发明涉及公式（I）的C-葡聚糖化合物，其中：S′是单糖基或从单糖或多糖S衍生的多糖基；R是直链或支链烷基基团；Z是乙烯基CH═CR1（R2）或乙炔基C≡CR3基团。该发明还涉及一种制备公式（III）的C-葡聚糖化合物的方法，其特征在于该方法包括以下反应模式：公式（II），（III）。
• A highly efficient and facile one pot synthesis of novel 1-glycopyranosyl-4-biaryl butenone derivatives
  作者：Kavita、Vipin K. Maikhuri、Harbansh Singla、Jyotirmoy Maity、Ashok K. Prasad

  DOI：10.1080/00397911.2023.2190461

  日期：——

  Abstract A facile and efficient methodology, comprised of a domino reaction, a Suzuki-Miyaura coupling reaction followed by an aldol condensation has been developed to synthesize novel 1-glycopyranosyl-4-biaryl butenone derivatives in a one-pot fashion. The reaction of C-glycosides 1-C-(β-D-glucosyl)propan-2-one, 1-C-(β-D-mannosyl)propan-2-one, 1-C-(β-D-galactosyl)propan-2-one, 1-C-(β-D-lactosyl)propan-2-one

  摘要 一种简便有效的方法，包括多米诺骨牌反应、Suzuki-Miyaura 偶联反应和随后的醛醇缩合，已经开发出来以一锅法合成新型 1-glycopyranosyl-4-biaryl butenone 衍生物。C-糖苷1- C -(β-D-glucosyl)propan-2-one, 1- C -(β-D-mannosyl)propan-2-one, 1- C -(β-D-galactosyl)的反应)propan-2-one, 1- C -(β-D-lactosyl)propan-2-one with 5-bromothiophene-2-carboxaldehyde or 4-bromobenzaldehyde and different boronic acids presence of Pd(II)-catalyst and室温下甲醇中的碱以 75-85% 的收率产生各种查尔酮型联苯C-糖苷。