3,5-di-O-benzoyl-2-deoxy-D-ribofuranose | 112137-63-0

• 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: 3,5-di-O-benzoyl-2-deoxy-D-ribofuranose
• 英文别名: 2-deoxy-3,5-O-dibenzoyl-D-ribofuranoside；3,5-di-O-benzoyl-2-deoxy-D-ribofuranoside；((2R,3S)-3-(Benzoyloxy)-5-hydroxytetrahydrofuran-2-yl)methyl benzoate；[(2R,3S)-3-benzoyloxy-5-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 112137-63-0
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: AKCFUIMCQPPMTA-RTKIROINSA-N

物化性质

• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-2-deoxy-D-ribofuranose 在 吡啶 、 二氯二茂铪 、 4 A molecular sieve 、 sodium methylate 、 silver perchlorate 、 N,N-二异丙基乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.83h， 生成
  参考文献：
  名称：

  Differential Solvation and Tautomer Stability of a Model Base Pair within the Minor and Major Grooves of DNA

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) may be used as a model base pair to study solvation, duplex environment, and tautomerization within the major and minor groves of DNA duplexes, In its ground state, HBO possesses an enol moiety which may be oriented syn or anti relative to the imino nitrogen of the benzoxazole ring. In the absence of external hydrogen-bond donors and acceptors HBO exists as the internally hydrogen-bonded syn-enol, a mimic of the rare base pair tautomer found in DNA, which may be photoinduced to tautomerize and form the keto tautomer, a mimic of the dominant base pair tautomer. Previously, we demonstrated that when incorporated into DNA such that the enol moiety is positioned in the major groove, HBO is not solvated, exists exclusively as the internally hydrogen-bonded syn-enol which is efficiently photoinduced to tautomerize, and the corresponding keto tautomer is preferentially stabilized. In stark contrast, we now show that when HBO is incorporated in DNA such that the enol moiety is positioned in the minor groove, the enol tautomer is preferentially stabilized. Molecular dynamics simulations suggest that this results from the formation of a stable hydrogen-bond between the HBO enol and the O4' atom of an adjacent nucleotide, an H-bond acceptor that is only available in the minor groove. The differential stabilization of the enol and keto tautomers in the major and minor grooves may reflect the functions for which these environments evolved, including duplex replication, stability, and recognition.

  DOI：

  10.1021/ja054607x
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三乙胺 、 乙酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.33h， 生成 3,5-di-O-benzoyl-2-deoxy-D-ribofuranose
  参考文献：
  名称：

  Differential Solvation and Tautomer Stability of a Model Base Pair within the Minor and Major Grooves of DNA

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) may be used as a model base pair to study solvation, duplex environment, and tautomerization within the major and minor groves of DNA duplexes, In its ground state, HBO possesses an enol moiety which may be oriented syn or anti relative to the imino nitrogen of the benzoxazole ring. In the absence of external hydrogen-bond donors and acceptors HBO exists as the internally hydrogen-bonded syn-enol, a mimic of the rare base pair tautomer found in DNA, which may be photoinduced to tautomerize and form the keto tautomer, a mimic of the dominant base pair tautomer. Previously, we demonstrated that when incorporated into DNA such that the enol moiety is positioned in the major groove, HBO is not solvated, exists exclusively as the internally hydrogen-bonded syn-enol which is efficiently photoinduced to tautomerize, and the corresponding keto tautomer is preferentially stabilized. In stark contrast, we now show that when HBO is incorporated in DNA such that the enol moiety is positioned in the minor groove, the enol tautomer is preferentially stabilized. Molecular dynamics simulations suggest that this results from the formation of a stable hydrogen-bond between the HBO enol and the O4' atom of an adjacent nucleotide, an H-bond acceptor that is only available in the minor groove. The differential stabilization of the enol and keto tautomers in the major and minor grooves may reflect the functions for which these environments evolved, including duplex replication, stability, and recognition.

  DOI：

  10.1021/ja054607x

文献信息

• Iron‐Catalyzed Radical Cleavage/C−C Bond Formation of Acetal‐Derived Alkylsilyl Peroxides
  作者：Yoko Shiozaki、Shunya Sakurai、Ryu Sakamoto、Akira Matsumoto、Keiji Maruoka

  DOI：10.1002/asia.201901695

  日期：2020.3.2

  selective cleavage of acetal-derived alkylsilyl peroxides, followed by the formation of a carbon-carbon bond is reported. The reaction proceeds under mild reaction conditions and exhibits a broad substrate scope with respect to the acetal moiety and the carbon electrophile. Mechanistic studies suggest that the present reaction proceeds through a free-radical process involving carbon radicals generated

  报道了一种基于自由基的新颖方法，用于铁催化的乙缩醛衍生的烷基甲硅烷基过氧化物的选择性裂解，然后形成碳-碳键。反应在温和的反应条件下进行，并且相对于缩醛部分和亲电碳表现出宽泛的底物范围。机理研究表明，本反应通过自由基过程进行，该自由基过程涉及由乙缩醛部分内碳-碳键的均相裂解产生的碳自由基。还描述了该方法在糖衍生的烷基甲硅烷基过氧化物中的合成应用。
• SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-ß-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
  申请人：FUJIFILM Corporation

  公开号：US20150152131A1

  公开（公告）日：2015-06-04

  A compound represented by a formula [1D] as shown below (wherein R 1A , R 1B , R 2A , R 2B , R 3A and R 3B represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, and the like) is useful as an intermediate for producing a thionucleoside, and the production method of the present invention is useful as a method for producing a thionucleoside.

  下列的化合物，其化学式为[1D]（其中R1A、R1B、R2A、R2B、R3A和R3B代表氢原子、可选择取代的C1-6烷基等），可作为生产硫代核苷的中间体，本发明的生产方法可作为一种生产硫代核苷的方法。
• 5 (S), 6(R)-5. 7-dibenzoyloxy-6-hydroxyheptanoate ester: improved synthesis of a leukotriene intermediate
  作者：D.P. Marriott、J.R. Bantick

  DOI：10.1016/s0040-4039(01)81985-7

  日期：1981.1

  The title compound, a key intermediate in the synthesis of leukotriene A4, was prepared by a convenient procedure from 2-deoxy-D-ribose.

  通过方便的方法由2-脱氧-D-核糖制备标题化合物，其为白三烯A 4合成中的关键中间体。
• Synthesis of an ethidium nucleoside and its acyclic analog
  作者：Nicole Amann、Hans-Achim Wagenknecht

  DOI：10.1016/s0040-4039(03)00025-x

  日期：2003.2

  The protected ethidium nucleosides 8-(3′,5′-di-O-benzoyl-2′-deoxy-d-ribofuranosyl)-3-acetamido-5-ethyl-6-phenyl-phenanthridinium (5), 8-(3′,5′-di-O-acetyl-2′-deoxy-d-ribofuranosyl)-3-acetamido-5-ethyl-6-phenyl-phenanthridinium (6), and the acyclic analog 8-[(3R)-1,3-dihydroxy-4-yl]-acetamido-3-amino-5-ethyl-6-phenyl-phenanthridinium (3) were prepared. Based on to their different stability, only the

  被保护的乙啶核苷8-（3'，5'-二-O-苯甲酰基-2'-脱氧-d-呋喃呋喃糖基）-3-乙酰氨基-5-乙基-6-苯基菲啶鎓（5），8-（3 ′，5′-二-O-乙酰基-2′-脱氧-d-呋喃核糖基）-3-乙酰氨基-5-乙基-6-苯基菲啶鎓（6），和无环类似物8-[（3 R）-制备1，3-二羟基-4-基]-乙酰胺基-3-氨基-5-乙基-6-苯基菲啶鎓（3）。基于它们的不同稳定性，仅无环衍生物3似乎适合于寡核苷酸合成。此外，无环乙啶核苷类似物3表现出与未衍生乙啶类似的吸收和发射性质（1）。
• １−（２−デオキシ−２−フルオロ−４−チオ−β−Ｄ−アラビノフラノシル）シトシンの合成中間体およびチオヌクレオシドの合成中間体ならびにそれらの製造法
  申请人：富士フイルム株式会社

  公开号：WO2014027658A1

  公开（公告）日：2014-02-20

  下記一般式［１Ｄ］（式中、Ｒ１Ａ、Ｒ１Ｂ、Ｒ２Ａ、Ｒ２Ｂ、Ｒ３ＡおよびＲ３Ｂは水素原子、置換されてもよいＣ１−６アルキル基などを示す。）で表される化合物は、チオヌクレオシドを製造するための中間体として有用であり、本発明の製造法はチオヌクレオシドの製造法として有用である。

  下列一般式［１Ｄ］（式中，Ｒ１Ａ、Ｒ１Ｂ、Ｒ２Ａ、Ｒ２Ｂ、Ｒ３Ａ和Ｒ３Ｂ表示氢原子，可取代的C1-6烷基等。）所表示的化合物，是作为制造硫代核苷的中间体而有用的，本发明的制造方法是制造硫代核苷的方法，因此具有实用性。