methyl 5-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pentofuranoside | 105386-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pentofuranoside
• 英文别名: methyl 5-O-(tert-butyldimethylsilyl)-2-deoxy-α,β-D-erythropentofuranoside；methyl 5-O-(t-butyldimethylsilyl)-2-deoxyribofuranoside；(2R,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methoxyoxolan-3-ol
• CAS: 105386-65-0
• 化学式: C₁₂H₂₆O₄Si
• 分子量: 262.422
• InChiKey: OLEJTHXINQTDOK-MTULOOOASA-N

物化性质

• 沸点：
  306.4±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pentofuranoside 在 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 Methyl 2-Deoxy-3-benzyl-D-ribofuranoside
  参考文献：
  名称：

  Highly Stereoselective Synthesis of 2′-Deoxy-α-ribonucleosides and 2-Deoxy-α-C-ribofuranosides by Remote Stereocontrolled Glycosylation

  摘要：

  通过利用 5-O-diethylthio carbamoyl 指导基团进行有效的远程立体控制，成功地开发了一种新的高效方法，用于催化 2-脱氧核糖衍生物与各种三甲基硅烷化亲核物进行高 α 选择性 N-和 C-糖基化反应。制备出了几种 2′-脱氧-α-核苷及其 C-类似物的前体，产量高，立体选择性强。

  DOI：

  10.1246/cl.1997.389
• 作为产物：
  描述：

  甲基-2-脱氧-D-核糖 以 吡啶 、 甲醇 、 氯仿 、 水 为溶剂， 生成 methyl 5-O-t-butyldimethylsilyl-2-deoxy-D-erythro-pentofuranoside
  参考文献：
  名称：

  2-deoxyuridines and riboside precursors

  摘要：

  提供了一种制备特定2-去氧尿嘧啶的过程，包括以下步骤：形成取代烷基5-O-"保护"的2-去氧核糖苷，通过烃基化后处理该化合物，然后在路易斯或布朗斯特德酸的存在下将烃基化化合物与硅基尿嘧啶缩合形成尿嘧啶。此外，几种三苯甲基化的核糖苷也是新的化合物。

  公开号：

  US04898936A1

文献信息

• Stereoselective β-<i>C</i>- and β-<i>S</i>-Glycosylation of 2-Deoxyribofuranose Derivatives Controlled by the 3-Hydroxy Protective Group
  作者：Yuh-ichiro Ichikawa、Hideki Kubota、Ken’ichi Fujita、Tatsuo Okauchi、Koichi Narasaka

  DOI：10.1246/bcsj.62.845

  日期：1989.3

  β-C-2-Deoxyribofuranosides and β-S-2-deoxyribofuranosides are prepared stereoselectively from 1-O-acetyl-5-O-benzyl-3-O-[2-(methylsulfinyl)ethyl]-2-deoxy-d-erythro-pentofuranose or the corresponding 3-O-(2-pyridyl-methyl)pentofuranose N-oxide by the reaction with silyl enol ethers or trimethlsilyl sulfides in the presence of a Lewis acid.

  β-C-2-脱氧核糖苷和β-S-2-脱氧核糖苷是通过与硅乙烯醚或三甲基硅基硫化物在路易斯酸存在下反应，从1-O-乙酰基-5-O-苄基-3-O-[2-(甲基亚砜基)乙基]-2-脱氧-d-赤藓糖和相应的3-O-(2-吡啶基-甲基)五碳呋喃糖N-氧化物立体选择性制备的。
• Sugar-Modified Foldamers as Conformationally Defined and Biologically Distinct Glycopeptide Mimics
  作者：Aloysius Siriwardena、Kiran Kumar Pulukuri、Pancham S. Kandiyal、Saumya Roy、Omprakash Bande、Subhash Ghosh、José Manuel Garcia Fernández、Fernando Ariel Martin、Jean-Marc Ghigo、Christophe Beloin、Keigo Ito、Robert J. Woods、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1002/anie.201304239

  日期：2013.9.23

  To fold or not to fold? It is shown that attached sugars play a defining role in the conformations adopted by a pair of novel SAA‐derived foldamers in water and that these differences are reflected in the contrasting interactions of these glycofoldamers with various biological targets. C green, O red, N blue, H gray; yellow oval=mannose.

  折叠还是不折叠？结果表明，附着的糖在水中一对新型 SAA 衍生折叠体所采用的构象中起着决定性作用，并且这些差异反映在这些糖折叠体与各种生物靶标的对比相互作用中。C绿、O红、N蓝、H灰；黄色椭圆形=甘露糖。
• A Synthetic Substrate of DNA Polymerase Deviating from the Bases, Sugar, and Leaving Group of Canonical Deoxynucleoside Triphosphates
  作者：Mi-Yeon Jang、Xiao-Ping Song、Mathy Froeyen、Philippe Marlière、Eveline Lescrinier、Jef Rozenski、Piet Herdewijn

  DOI：10.1016/j.chembiol.2013.02.010

  日期：2013.3

  The selection of artificial nucleic acids to be used for synthetic biology purposes is based on their structural and biochemical orthogonality to the natural system. We describe the example of a nucleotide mimic that functions as a substrate for polymerases and in which the carbohydrate moiety as well as the base moiety and the leaving group are different from that of the natural building blocks. The nucleotides themselves have two anomeric centers, and different leaving group properties of substituents at both anomeric centers need to be exploited to perform selective glycosylation reactions for their synthesis. In addition, the reversibility of the polymerase reaction at the level of the template has been demonstrated when pyrophosphate functions as leaving group and not with the alternative leaving groups.
• Synthesis of 2‘,5‘-Dideoxy-2-fluoroadenosine and 2‘,5‘-Dideoxy-2,5‘-difluoroadenosine:  Potent P-Site Inhibitors of Adenylyl Cyclase
  作者：Song Ye、Martha M. Rezende、Wei-Ping Deng、Brian Herbert、John W. Daly、Roger A. Johnson、Kenneth L. Kirk

  DOI：10.1021/jm0303599

  日期：2004.2.1

  Glycosylation of 2-fluoroadenine with the appropriate protected thioglycoside derivatives, followed by deprotection and anomer separation, produced the alpha- and beta-anomers of 2',5'-dideoxy-2-fluoroadenosine (1), 2',5'-dideoxy-2,5'-difluoroadenosine (2), and 2'-deoxy-2-fluoroadenosine (3). These were examined as P-site inhibitors of adenylyl cyclase. The presence of fluorine on the purine ring increased potency of inhibition, and the most potent compound, beta-2',5'-dideoxy-2-fluoroadenosine (1b), was 3 times more potent than beta-2',5'-dideoxyadenosine.
• Highly Stereoselective Synthesis of 2′-Deoxy-<i>α</i>-ribonucleosides and 2-Deoxy-<i>α</i>-C-ribofuranosides by Remote Stereocontrolled Glycosylation
  作者：Teruaki Mukaiyama、Tatsuya Ishikawa、Hiromi Uchiro

  DOI：10.1246/cl.1997.389

  日期：1997.4

  A new and efficient method for catalytic highly α-selective N- and C-glycosylations of 2-deoxyribose derivative with various trimethylsilylated nucleophiles was successfully developed by utilizing effective remote stereocontrol with 5-O-diethylthio carbamoyl directing group. Several 2′-deoxy-α-ribonucleosides and precursors of its C-analogues were prepared in good yields with high stereoselectivities.

  通过利用 5-O-diethylthio carbamoyl 指导基团进行有效的远程立体控制，成功地开发了一种新的高效方法，用于催化 2-脱氧核糖衍生物与各种三甲基硅烷化亲核物进行高 α 选择性 N-和 C-糖基化反应。制备出了几种 2′-脱氧-α-核苷及其 C-类似物的前体，产量高，立体选择性强。