(1R,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane | 113299-36-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane
• 英文别名: 1,2,3,5-Tetra-O-acetylcarba-α-D-xylofuranose；[(1R,2S,3S,4S)-2,3,4-triacetyloxycyclopentyl]methyl acetate
• CAS: 113299-36-8
• 化学式: C₁₄H₂₀O₈
• 分子量: 316.308
• InChiKey: MSZKNSYGZGPKPT-RFGFWPKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以83%的产率得到(1R,2S,3S,4S)-2,3,4-trihydroxy-1-(hydroxymethyl)cyclopentane
  参考文献：
  名称：

  Synthesis of All Stereoisomeric Carbapentofuranoses

  摘要：

  All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer-Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyre, and alpha-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3-position was found. If an epoxy acetate with both functions on the same side of the ring was used, the epoxide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.

  DOI：

  10.1021/jo00121a046
• 作为产物：
  描述：

  (1S,2S,4S)-4-(t-butyldiphenylsilyloxymethyl)-1,2-isopropylidenedioxy-3-cyclopentanone 在 吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 silica gel 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 348.5h， 生成 (1R,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane
  参考文献：
  名称：

  Transformation of D-erythrose to some pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-trihydroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine

  摘要：

  DOI：

  10.1021/jo00242a016

文献信息

• TADANO, KIN-ICHI;HOSHINO, MASAHIDE;OGAWA, SEIICHIRO;SUAMI, TETSUO, J. ORG. CHEM., 53,(1988) N 7, 1427-1432
  作者：TADANO, KIN-ICHI、HOSHINO, MASAHIDE、OGAWA, SEIICHIRO、SUAMI, TETSUO

  DOI：——

  日期：——