(1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol | 115094-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol
• 英文别名: (1S,2R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethoxy-3-[[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]but-3-en-2-ol
• CAS: 115094-69-4
• 化学式: C₅₁H₅₈O₉
• 分子量: 815.016
• InChiKey: LBCANSCAIZUQCH-YCNYGRQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  60
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol 在 吡啶 、 咪唑 、 四氧化锇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1S,2S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-[(S)-2-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-ethanol
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 11. C-Sucrose: new practical synthesis, structural reassignment, and solid-state and solution conformation of its octaacetate

  摘要：

  The stereochemistry of C-sucrose, previously reported from this laboratory, was revised as epi-C.2'-C-sucrose (5) from H-1 NOE measurements on octaacetates 2 and 6 and an X-ray analysis of 2. A new, stereospecific, and practical synthesis of C-sucrose (1) was developed. The solid-state conformation and solution behavior of the octaacetate 2 of C-sucrose were compared with the corresponding octaacetate 4 of parent sucrose.

  DOI：

  10.1021/jo00054a006
• 作为产物：
  描述：

  (1S,2S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-phenylmethoxy-3-[[(2R,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]but-3-en-2-ol 生成 (1S,2R)-1-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-but-3-en-2-ol
  参考文献：
  名称：

  DYER, U. C.;KISHI, YOSHITO, J. ORG. CHEM., 53,(1988) N 14, 3383-3384

  摘要：

  DOI：

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.
• DYER, U. C.;KISHI, YOSHITO, J. ORG. CHEM., 53,(1988) N 14, 3383-3384
  作者：DYER, U. C.、KISHI, YOSHITO

  DOI：——

  日期：——
• Synthesis of C-sucrose
  作者：Ulrich C. Dyer、Yoshito Kishi

  DOI：10.1021/jo00249a056

  日期：1988.7
• Preferred conformation of C-glycosides. 11. C-Sucrose: new practical synthesis, structural reassignment, and solid-state and solution conformation of its octaacetate
  作者：Daniel J. O'Leary、Yoshito Kishi

  DOI：10.1021/jo00054a006

  日期：1993.1

  The stereochemistry of C-sucrose, previously reported from this laboratory, was revised as epi-C.2'-C-sucrose (5) from H-1 NOE measurements on octaacetates 2 and 6 and an X-ray analysis of 2. A new, stereospecific, and practical synthesis of C-sucrose (1) was developed. The solid-state conformation and solution behavior of the octaacetate 2 of C-sucrose were compared with the corresponding octaacetate 4 of parent sucrose.