(S)-1-((2R,4R,6R)-6-allyl-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)ethane-1,2-diol | 1400695-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (S)-1-((2R,4R,6R)-6-allyl-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)ethane-1,2-diol
• 英文别名: (1S)-1-[(2R,4R,6R)-4-methoxy-5,5-dimethyl-6-prop-2-enyloxan-2-yl]ethane-1,2-diol
• CAS: 1400695-36-4
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: RWIWOIYGGQMBEC-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-((2R,4R,6R)-6-allyl-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)ethane-1,2-diol 在 sodium hypochlorite 、 sodium chlorite 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 aq. phosphate buffer 、 乙醚 、 乙腈 为溶剂， 反应 24.0h， 生成 (R)-methyl 2-((2R,4R,6R)-methyl-6-allyl-4-methoxy-5,5-dimethyltetrahydro-2H-pyran-2-yl)hydroxylacetate
  参考文献：
  名称：

  Organocatalytic One-Pot Oxidative Cleavage of Terminal Diols to Dehomologated Carboxylic Acids

  摘要：

  The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO2 caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.

  DOI：

  10.1021/ol3021429

文献信息

• Nitroxyl Radical/PhI(OAc)₂: One-Pot Oxidative Cleavage of Vicinal Diols to (Di)Carboxylic Acids
  作者：Masatoshi Shibuya、Takuro Shibuta、Hayato Fukuda、Yoshiharu Iwabuchi

  DOI：10.1021/ol3021435

  日期：2012.10.5

  corresponding (di)carboxylic acids using AZADOs and PhI(OAc)2 is described. 1,2-Diols and 2,3-diols as well as 1,2,3-triol gave one- or two-carbon-unit-shorter carboxylic acids. Internal vicinal diols also smoothly underwent one-pot oxidative cleavage to afford the corresponding dicarboxylic acids. Cyclic vicinal diols are converted to their corresponding open-form dicarboxylic acids.

  描述了使用AZADO和PhI（OAc）2对邻二醇进行温和且易于使用的一锅氧化裂解为相应的（二）羧酸的方法。1,2-二醇和2,3-二醇以及1,2,3-三醇生成一个或两个碳单元短的羧酸。内部邻位二醇也顺利进行一锅氧化裂解，得到相应的二羧酸。环状邻位二醇被转化为其相应的开放形式二元羧酸。