2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal | 153439-75-9

• 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: 2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal
• 英文别名: (2R,3R,4R)-5,5-bis(benzylsulfanyl)-1,3,4-tris(phenylmethoxy)pentan-2-ol
• CAS: 153439-75-9
• 化学式: C₄₀H₄₂O₄S₂
• 分子量: 650.903
• InChiKey: XVAQPCSGOYVDDU-CCUSMBMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  46
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal 在 吡啶 、 四丁基碘化铵 、 barium carbonate 作用下， 反应 26.0h， 生成 benzyl 2,3,5-tri-O-benzyl-1,4-dithio-L-lyxofuranoside
  参考文献：
  名称：

  硫糖。VIII.*新的 4'-硫代-L-赖氨酸嘧啶核苷类似物的制备

  摘要：

  1-O-乙酰基-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 与甲硅烷基化嘧啶碱基反应，随后用三溴化硼脱保护，生成 4'-thio-L-lyxo 嘧啶核苷。5-溴-6-甲基衍生物由甲基 2,3,5-三-O-乙酰-4-硫代-L-lyxofuranoside 制备。用甲醇钠进行脱乙酰。端基异构体通过 HPLC 分离，并通过 NMR 光谱和 X 射线结构分析确定其构型。测试了核苷的生物活性。*第七部分：Wirsching, J.、Voss, J.、Adiwidjaja, G.、Giesler, A.、Kopf, J. Eur。J. 组织 化学 2001 年，印刷中。

  DOI：

  10.1081/ncn-100105900
• 作为产物：
  描述：

  甲基 2,3,5-三-O-苄基-D-呋喃核糖苷 、 苄硫醇 在 三氟化硼乙醚 作用下， 反应 48.0h， 以75%的产率得到2,3,5-tri-O-benzyl-D-ribose dibenzyldithioacetal
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205

文献信息

• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。
• A Stereoselective Approach to Nucleosides and 4′-Thioanalogues from Acyclic Precursors
  作者：Daniel Chapdelaine、Benoit Cardinal-David、Michel Prévost、Marc Gagnon、Isabelle Thumin、Yvan Guindon

  DOI：10.1021/ja905452f

  日期：2009.12.2

  D- and L-nucleosides and analogues thereof, including the 4'-thionucleoside series, are one of the most important biological and pharmaceutically active classes of compounds. A novel approach to their synthesis from chiral acyclic thioaminal, bearing the nucleobase, is described.
• Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine¹
  作者：Kamal N. Tiwari、John A. Secrist、John A. Montgomery

  DOI：10.1080/15257779408009484

  日期：1994.9

  1,2,3,5-Tetra-O-acetyl-4-thio-D-ribofuranose,prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2'-deoxy-4'-thioadenosine (12). This is the first report of a 2'-deoxy-4'-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoxic to several human tumor cell lines in culture.