2-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-ethanol | 1053652-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-ethanol
• 英文别名: 2-[(2S,4S,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]ethanol
• CAS: 1053652-61-1
• 化学式: C₂₁H₂₆O₄
• 分子量: 342.435
• InChiKey: QCDCWEBNIFRRKE-PCCBWWKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-ethanol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 生成 β-C-2-Deoxyribofuranoside
  参考文献：
  名称：

  Preferred Conformation of C-Glycosides. 13. A Comparison of the Conformational Behavior of Several C-, N-, and O-Furanosides

  摘要：

  A qualitative comparison of C-furanosides, derived from arabinose and 2-deoxyribose, with the naturally occurring O- and N-furanosides was performed using solution H-1 NMR spectroscopy and X-ray crystallography. The ring conformations of beta- and alpha-C-arabino and beta- and alpha-C-2-deoxyribofuranosides tend to possess equatorial anomeric C-C bonds, in contrast to the O-furanosides, which have ring conformations stabilized by axial anomeric C-O bonds due to a stereoelectronic effect. Installation of a quaternary anomeric center in C-furanosides introduces unfavorable 1,3-diaxial-like steric interactions, which can shift the ring conformational equilibrium in such a manner that the C-furanoside becomes more similar to the O-furanoside. The solid-state conformation of the C-nucleoside beta-arabinosyl pseudouridine was shown to be virtually identical to N-nucleoside beta-arabinosyluridine. In solution, however, the ring conformation of this N-furanoside, and its 2-deoxy analog, is intermediate to the corresponding oxygen- and carbon-derived entries. When compared to C-pyranosides, C-furanosides seem to have anomeric linkages prone to increased exo-anomeric conformational averaging. A quaternary furanosyl anomeric center such as in O-sucrose (1) and C-sucrose (2) appears to provide further flexibility at this anomeric linkage. Evidence is provided which suggests the flexible nature of sucrose arises at the fructofuranosyl linkage, as the glucopyranosyl linkage in this compound is conformationally well-defined in the exo-anomeric sense. The analysis of the preferred syn/anti base conformation in C-nucleosides can be complicated by a stronger equatorial base preference.

  DOI：

  10.1021/jo00101a022
• 作为产物：
  描述：

  3O,5O-dibenzyl-2-deoxy-1,4-ribonolactone 在 三乙基硅烷 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-((2S,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-ethanol
  参考文献：
  名称：

  Preferred Conformation of C-Glycosides. 13. A Comparison of the Conformational Behavior of Several C-, N-, and O-Furanosides

  摘要：

  A qualitative comparison of C-furanosides, derived from arabinose and 2-deoxyribose, with the naturally occurring O- and N-furanosides was performed using solution H-1 NMR spectroscopy and X-ray crystallography. The ring conformations of beta- and alpha-C-arabino and beta- and alpha-C-2-deoxyribofuranosides tend to possess equatorial anomeric C-C bonds, in contrast to the O-furanosides, which have ring conformations stabilized by axial anomeric C-O bonds due to a stereoelectronic effect. Installation of a quaternary anomeric center in C-furanosides introduces unfavorable 1,3-diaxial-like steric interactions, which can shift the ring conformational equilibrium in such a manner that the C-furanoside becomes more similar to the O-furanoside. The solid-state conformation of the C-nucleoside beta-arabinosyl pseudouridine was shown to be virtually identical to N-nucleoside beta-arabinosyluridine. In solution, however, the ring conformation of this N-furanoside, and its 2-deoxy analog, is intermediate to the corresponding oxygen- and carbon-derived entries. When compared to C-pyranosides, C-furanosides seem to have anomeric linkages prone to increased exo-anomeric conformational averaging. A quaternary furanosyl anomeric center such as in O-sucrose (1) and C-sucrose (2) appears to provide further flexibility at this anomeric linkage. Evidence is provided which suggests the flexible nature of sucrose arises at the fructofuranosyl linkage, as the glucopyranosyl linkage in this compound is conformationally well-defined in the exo-anomeric sense. The analysis of the preferred syn/anti base conformation in C-nucleosides can be complicated by a stronger equatorial base preference.

  DOI：

  10.1021/jo00101a022

文献信息

• Preferred Conformation of C-Glycosides. 13. A Comparison of the Conformational Behavior of Several C-, N-, and O-Furanosides
  作者：Daniel J. O'Leary、Yoshito Kishi

  DOI：10.1021/jo00101a022

  日期：1994.11

  A qualitative comparison of C-furanosides, derived from arabinose and 2-deoxyribose, with the naturally occurring O- and N-furanosides was performed using solution H-1 NMR spectroscopy and X-ray crystallography. The ring conformations of beta- and alpha-C-arabino and beta- and alpha-C-2-deoxyribofuranosides tend to possess equatorial anomeric C-C bonds, in contrast to the O-furanosides, which have ring conformations stabilized by axial anomeric C-O bonds due to a stereoelectronic effect. Installation of a quaternary anomeric center in C-furanosides introduces unfavorable 1,3-diaxial-like steric interactions, which can shift the ring conformational equilibrium in such a manner that the C-furanoside becomes more similar to the O-furanoside. The solid-state conformation of the C-nucleoside beta-arabinosyl pseudouridine was shown to be virtually identical to N-nucleoside beta-arabinosyluridine. In solution, however, the ring conformation of this N-furanoside, and its 2-deoxy analog, is intermediate to the corresponding oxygen- and carbon-derived entries. When compared to C-pyranosides, C-furanosides seem to have anomeric linkages prone to increased exo-anomeric conformational averaging. A quaternary furanosyl anomeric center such as in O-sucrose (1) and C-sucrose (2) appears to provide further flexibility at this anomeric linkage. Evidence is provided which suggests the flexible nature of sucrose arises at the fructofuranosyl linkage, as the glucopyranosyl linkage in this compound is conformationally well-defined in the exo-anomeric sense. The analysis of the preferred syn/anti base conformation in C-nucleosides can be complicated by a stronger equatorial base preference.