5-O-<(tert-butyl)diphenylsilyl>-2-deoxy-3,4-O-isopropylidene-aldehydo-D-ribose | 135821-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-<(tert-butyl)diphenylsilyl>-2-deoxy-3,4-O-isopropylidene-aldehydo-D-ribose
• 英文别名: 5-O-[(tert-butyl)diphenylsilyl]-2-deoxy-3,4-O-isopropylidene-aldehydo-D-ribose；2-[(4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde
• CAS: 135821-12-4
• 化学式: C₂₄H₃₂O₄Si
• 分子量: 412.601
• InChiKey: LCTMCKGCOLNNJV-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-O-<(tert-butyl)diphenylsilyl>-2-deoxy-3,4-O-isopropylidene-aldehydo-D-ribose 在 吡啶 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.25h， 生成 (2-amino-2-methylpropyl) 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-4-carboxylate
  参考文献：
  名称：

  2-（2-脱氧-β-D-核呋喃呋喃糖基）吡啶-4-羧酰胺的合成及生物评价†

  摘要：

  从以下步骤开始合成了一种新的受保护的2-脱氧-D-核糖衍生物5- O -[（叔丁基）二苯基甲硅烷基] -2-脱氧-3,4 - O-异亚丙基-醛-D-核糖（5） 2-脱氧-D-核糖。将该化合物与2-硫代-4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶偶联，得到5- O -[（叔丁基）的D / L-甘油混合物7。二苯基甲硅烷基] -2-脱氧-1- C- [4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶-2-基] -3,4- O-异亚丙基-D-赤-戊糖醇。混合物7为1- O用甲磺酰氯甲磺酰化，然后用CF 3 COOH / H 2 O和氨处理得到2-（2-脱氧-D-呋喃核糖基）吡啶-4-甲酰胺的α/β-D-端基异构体10。两种端基异构体均通过HPLC纯化和分离，并通过NMR和DCI-MS鉴定。针对一系列肿瘤细胞系和各种病毒株评估了异构体β-D- 10。没有观察到抗肿瘤或抗病毒活性。

  DOI：

  10.1002/hlca.19920750516
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 咪唑 、 盐酸 、 对甲苯磺酸 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 23.33h， 生成 5-O-<(tert-butyl)diphenylsilyl>-2-deoxy-3,4-O-isopropylidene-aldehydo-D-ribose
  参考文献：
  名称：

  2-（2-脱氧-β-D-核呋喃呋喃糖基）吡啶-4-羧酰胺的合成及生物评价†

  摘要：

  从以下步骤开始合成了一种新的受保护的2-脱氧-D-核糖衍生物5- O -[（叔丁基）二苯基甲硅烷基] -2-脱氧-3,4 - O-异亚丙基-醛-D-核糖（5） 2-脱氧-D-核糖。将该化合物与2-硫代-4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶偶联，得到5- O -[（叔丁基）的D / L-甘油混合物7。二苯基甲硅烷基] -2-脱氧-1- C- [4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶-2-基] -3,4- O-异亚丙基-D-赤-戊糖醇。混合物7为1- O用甲磺酰氯甲磺酰化，然后用CF 3 COOH / H 2 O和氨处理得到2-（2-脱氧-D-呋喃核糖基）吡啶-4-甲酰胺的α/β-D-端基异构体10。两种端基异构体均通过HPLC纯化和分离，并通过NMR和DCI-MS鉴定。针对一系列肿瘤细胞系和各种病毒株评估了异构体β-D- 10。没有观察到抗肿瘤或抗病毒活性。

  DOI：

  10.1002/hlca.19920750516

文献信息

• Efficient Synthesis of α- and β-2′-Deoxy-heteroaryl-<i>C</i>-nucleosides
  作者：Alain Burger、Rachid Benhida、Marie Spadafora

  DOI：10.1055/s-2008-1072589

  日期：2008.5

  A short and efficient method for the synthesis of a series of 2′-deoxy-heteroaryl- C-nucleosides has been developed by the application of aryl-aldol condensation followed by P-toluenesulfonic acid (PTSA)-mediated isopropylidene cleavage and subsequent cycloetherification.

  通过应用芳基-羟醛缩合，然后对甲苯磺酸 (PTSA) 介导的异亚丙基裂解和随后的环醚化，开发了一种短而有效的合成一系列 2'-脱氧-杂芳基-C-核苷的方法。
• Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases
  作者：Marie Spadafora、Victoria Y. Postupalenko、Volodymyr V. Shvadchak、Andrey S. Klymchenko、Yves Mély、Alain Burger、Rachid Benhida

  DOI：10.1016/j.tet.2009.07.021

  日期：2009.9

  The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside la bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside la displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-<i>C</i>-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase
  作者：Dominique Guianvarc'h、Jean-Louis Fourrey、Rosalie Maurisse、Jian-Sheng Sun、Rachid Benhida

  DOI：10.1021/ol026609h

  日期：2002.11.1

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.
• Asymmetric Total Synthesis of Bioactive Natural Lipid Mycalol
  作者：Subhendu Das、Tapan Kumar Kuilya、Rajib Kumar Goswami

  DOI：10.1021/acs.joc.5b00972

  日期：2015.6.19

  A concise and convergent route for stereoselective total synthesis of promising anticancer natural lipid mycalol has been achieved using cheap and readily available L-arabinose as a chiral pool. The notable features of our synthesis comprised regioselective Wacker oxidation, Sharpless asymmetric dihydroxylation, Julia-Kocienski olefination, Wittig olefination, Zipper reaction, and Sonogashira reaction. Comparison of the spectroscopic data on a series of isomers supports the revised structure (Org. Lett. 2015, 17, 1652) instead of the one originally proposed.
• Synthesis and Biological Evaluation of 2-(2-Deoxy-?-D-ribofuranosyl)pyridine-4-carboxamide
  作者：Pieter E. Joos、Eddy L. Esmans、Roger A. Dommisse、Andr� De Bruyn、Jan M. Balzarini、Eric D. De Clercq

  DOI：10.1002/hlca.19920750516

  日期：1992.8.13

  1-O-mesylated with methanesulfonyl chloride and subsequently treated with CF3COOH/H2O and ammonia to afford the α/β-D-anomers 10 of 2-(2-deoxy-D-ribofuranosyl)pyridine-4-carboxamide. Both anomers were purified and separated by HPLC and identified by NMR and DCI-MS. Anomer β-D-10 was evaluated against a series of tumor-cell lines and a variety of viral strains. No antitumor or antiviral activity was observed.

  从以下步骤开始合成了一种新的受保护的2-脱氧-D-核糖衍生物5- O -[（叔丁基）二苯基甲硅烷基] -2-脱氧-3,4 - O-异亚丙基-醛-D-核糖（5） 2-脱氧-D-核糖。将该化合物与2-硫代-4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶偶联，得到5- O -[（叔丁基）的D / L-甘油混合物7。二苯基甲硅烷基] -2-脱氧-1- C- [4-（4,5-二氢-4,4-二甲基恶唑-2-基）吡啶-2-基] -3,4- O-异亚丙基-D-赤-戊糖醇。混合物7为1- O用甲磺酰氯甲磺酰化，然后用CF 3 COOH / H 2 O和氨处理得到2-（2-脱氧-D-呋喃核糖基）吡啶-4-甲酰胺的α/β-D-端基异构体10。两种端基异构体均通过HPLC纯化和分离，并通过NMR和DCI-MS鉴定。针对一系列肿瘤细胞系和各种病毒株评估了异构体β-D- 10。没有观察到抗肿瘤或抗病毒活性。