4,6-di-O-benzyl-3-deoxy-2-O-p-toluenesulfonyl-1,5-anhydro-D-arabinohexitol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-di-O-benzyl-3-deoxy-2-O-p-toluenesulfonyl-1,5-anhydro-D-arabinohexitol
• 英文别名: [(3S,5S,6R)-5-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] 4-methylbenzenesulfonate
• 化学式: C₂₇H₃₀O₆S
• 分子量: 482.598
• InChiKey: PBHPXNJDDAXURQ-DOEKTCAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-di-O-benzyl-3-deoxy-2-O-p-toluenesulfonyl-1,5-anhydro-D-arabinohexitol 在 吡啶 、 三甲基氯硅烷 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、137.9 kPa 条件下， 反应 53.5h， 生成 3′-deoxy-2′-(N(6)-benzoyladenin-9-yl)-1′,5′-anhydro-D-ribo-hexitol
  参考文献：
  名称：

  1′,5′-Anhydro-l-ribo-hexitol Adenine Nucleic Acids (α-l-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World

  摘要：

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.

  DOI：

  10.1021/acs.joc.5b00406
• 作为产物：
  描述：

  (2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 mercury(II) diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 56.5h， 生成 4,6-di-O-benzyl-3-deoxy-2-O-p-toluenesulfonyl-1,5-anhydro-D-arabinohexitol
  参考文献：
  名称：

  1′,5′-Anhydro-l-ribo-hexitol Adenine Nucleic Acids (α-l-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World

  摘要：

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.

  DOI：

  10.1021/acs.joc.5b00406

文献信息

• Synthesis and Antiviral Activity of the α-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-<scp>d</scp>-ribohexitol Nucleosides)
  作者：Nafizal Hossain、Jef Rozenski、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jo961982m

  日期：1997.4.1

  1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a C-4(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types I and 2.
• 1′,5′-Anhydro-<scp>l</scp>-<i>ribo</i>-hexitol Adenine Nucleic Acids (α-<scp>l</scp>-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World
  作者：Daniele D’Alonzo、Mathy Froeyen、Guy Schepers、Giovanni Di Fabio、Arthur Van Aerschot、Piet Herdewijn、Giovanni Palumbo、Annalisa Guaragna

  DOI：10.1021/acs.joc.5b00406

  日期：2015.5.15

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.