toluene-4-sulfonic acid (4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

• 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: toluene-4-sulfonic acid (4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• 英文别名: (4aR,7S,8aS) toluene-4-sulfonic acid 2-phenyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl ester；[(4aR,7S,8aS)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate
• 化学式: C₂₀H₂₂O₆S
• 分子量: 390.457
• InChiKey: XKHHGLKVQIEAKW-DAABDDCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  toluene-4-sulfonic acid (4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 吡啶 、 sodium hydroxide 、 三甲基氯硅烷 、 12-冠醚-4 、 lithium hydride 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 3′-deoxy-2′-(N(6)-benzoyladenin-9-yl)-1′,5′-anhydro-D-ribo-hexitol
  参考文献：
  名称：

  Hybridization between “Six-Membered” Nucleic Acids:  RNA as a Universal Information System

  摘要：

  [GRAPHICS]Within the polyA:polyT recognition system, cross-pairing between several nucleic acids with a phosphorylated six-membered carbohydrate (mimic) as repeating unit in the backbone structure has been observed. All investigated nucleic acids (except for beta -homo-DNA) hybridize with RNA, leaving RNA as a versatile biopolymer for informational transfer.

  DOI：

  10.1021/ol016183r
• 作为产物：
  描述：

  1,5-脱水-3-脱氧-4,6-O-(苯基亚甲基)-D-核-己糖醇 在 吡啶 、 氨 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 toluene-4-sulfonic acid (4aR,7S,8aS)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
  参考文献：
  名称：

  Hybridization between “Six-Membered” Nucleic Acids:  RNA as a Universal Information System

  摘要：

  [GRAPHICS]Within the polyA:polyT recognition system, cross-pairing between several nucleic acids with a phosphorylated six-membered carbohydrate (mimic) as repeating unit in the backbone structure has been observed. All investigated nucleic acids (except for beta -homo-DNA) hybridize with RNA, leaving RNA as a versatile biopolymer for informational transfer.

  DOI：

  10.1021/ol016183r

文献信息

• [EN] METHOD OF PREPARATION OF NOVEL NUCLEOSIDE ANALOGS AND USES<br/>[FR] PROCEDE POUR PREPARER DE NOUVEAUX ANALOGUES DE NUCLEOSIDE, ET LEURS UTILISATIONS
  申请人：AUSPEX PHARMACEUTICALS INC

  公开号：WO2005049582A1

  公开（公告）日：2005-06-02

  Processes for the preparation of racemic and optically active nucleoside analogs of formula (A) are described. These compounds are useful as anti-infective agents, antisense therapeutic agents and hybridization assay probes.

  描述了制备式(A)的外消旋和光学活性核苷类似物的过程。这些化合物可用作抗感染剂、反义治疗剂和杂交分析探针。
• Method of preparation of novel nucleoside analogs and uses
  申请人：Tse Bruno

  公开号：US20110070192A1

  公开（公告）日：2011-03-24

  Processes for the preparation of racemic and optically active nucleoside analogs of formula (A) are described. These compounds are useful as anti-infective agents, antisense therapeutic agents and hybridization assay probes.

  本文描述了制备式（A）的外消旋和光学活性核苷类似物的过程。这些化合物可用作抗感染剂，反义治疗剂和杂交检测探针。
• 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.
• Hybridization between “Six-Membered” Nucleic Acids:  RNA as a Universal Information System
  作者：Luc Kerremans、Guy Schepers、Jef Rozenski、Roger Busson、Arthur Van Aerschot、Piet Herdewijn

  DOI：10.1021/ol016183r

  日期：2001.12.1

  [GRAPHICS]Within the polyA:polyT recognition system, cross-pairing between several nucleic acids with a phosphorylated six-membered carbohydrate (mimic) as repeating unit in the backbone structure has been observed. All investigated nucleic acids (except for beta -homo-DNA) hybridize with RNA, leaving RNA as a versatile biopolymer for informational transfer.