1,2-dideoxy-D-glycero-L-manno-oct-1-enitol | 866413-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2-dideoxy-D-glycero-L-manno-oct-1-enitol
• 英文别名: (2R,3S,4R,5S,6S)-oct-7-ene-1,2,3,4,5,6-hexol
• CAS: 866413-95-8
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: JZGSGLXIHQVWFJ-GWVFRZDISA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethanol (64-17-5))
• 沸点：
  534.6±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-D-glycero-L-manno-oct-1-enitol 在 臭氧 、 二甲基硫 作用下， 以 甲醇 为溶剂， 生成 D-glycero-α-L-manno-heptose 、 D-glycero-α-L-manno-heptose
  参考文献：
  名称：

  Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

  摘要：

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.

  DOI：

  10.1021/jo051297s
• 作为产物：
  描述：

  D-来苏糖 在 indium 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 1,2-dideoxy-D-glycero-L-manno-oct-1-enitol
  参考文献：
  名称：

  Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

  摘要：

  A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.

  DOI：

  10.1021/jo051297s

文献信息

• Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides
  作者：Riccardo Cribiù、Ian Cumpstey

  DOI：10.1039/b718060h

  日期：——

  Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA-acetonitrile-toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans.

  用TFA-乙腈-甲苯处理后，含有烯丙基醇，醚或酯官能团的苄基醚保护的多羟基化烯烃化合物经历立体有择的环化反应，其中烯丙基位置上的构型反转并且苄基醚损失而得到四氢呋喃。