2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine | 137233-57-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine
• 英文别名: 2',3'-bis(O-tert-butyldimethylsilyl)-3-(p-methoxybenzyl)uridine；1-[(2R,3R,4R,5R)-3,4-bis{[tert-Butyl(dimethyl)silyl]oxy}-5-(hydroxymethyl)tetrahydro-2-furanyl]-3-(4-methoxybenzyl)-2,4(1H,3H)-pyrimidinedione；1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-(hydroxymethyl)oxolan-2-yl]-3-[(4-methoxyphenyl)methyl]pyrimidine-2,4-dione
• CAS: 137233-57-9
• 化学式: C₂₉H₄₈N₂O₇Si₂
• 分子量: 592.88
• InChiKey: YVYMQTGVBZIIRG-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine 在 吡啶 、 盐酸 、 potassium fluoride 、 草酰氯 、 ammonium cerium(IV) nitrate 、 三乙基硼 、 三正丁基氢锡 、 二甲基亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 23.42h， 生成 5'-epi-tunicaminyluracil
  参考文献：
  名称：

  Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V

  摘要：

  A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

  DOI：

  10.1021/ja00090a018
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 咪唑 、 sodium hydride 、 苯磺酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.08h， 生成 2',3'-O-bis(tert-butyldimethylsilyl)-3-N-(p-methoxybenzyl)uridine
  参考文献：
  名称：

  Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V

  摘要：

  A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

  DOI：

  10.1021/ja00090a018

文献信息

• Stereoselective Synthesis of Uridine-Derived Nucleosyl Amino Acids
  作者：Anatol P. Spork、Daniel Wiegmann、Markus Granitzka、Dietmar Stalke、Christian Ducho

  DOI：10.1021/jo201935w

  日期：2011.12.16

  nucleosyl amino acids (NAAs) represent simplified analogues of the core structure of muraymycin nucleoside antibiotics, making them useful synthetic building blocks for structure–activity relationship (SAR) studies. The key step of the developed synthetic route was the efficient and highly diastereoselective asymmetric hydrogenation of didehydro amino acid precursors toward protected NAAs. It was anticipated

  构想并合成了5'-脱氧尿苷和甘氨酸的新型杂合结构。此类核苷氨基酸（NAA）代表穆来霉素核苷抗生素核心结构的简化类似物，使其成为结构与活性关系（SAR）研究的有用合成构件。已开发的合成路线的关键步骤是将二脱氢氨基酸前体高效且高度非对映选择性地不对称氢化成受保护的NAA。预期通过该途径合成未保护的穆雷霉素衍生物将需要在尿嘧啶碱基的N-3处具有合适的中间保护基。在最初尝试使用PMB-和BOM-N-3保护后，这两个步骤都导致了脱保护步骤的问题，然后构想出N-3无保护基团的路线。尽管尿嘧啶-3-NH具有明显的酸性，但该途径与涉及N-3保护的初始策略一样有效，立体选择性也相同。所获得的NAA构件被用于合成截短的5'-脱氧村霉素类似物。
• Improved Convergent Synthesis of 5′-epi-Analogues of Muraymycin Nucleoside Antibiotics
  作者：Christian Ducho、Anatol Spork、Stefan Koppermann

  DOI：10.1055/s-0029-1217742

  日期：2009.9

  Nucleoside antibiotics represent a promising class of natural products for the development of novel antibacterial agents, with particular respect to structurally simplified analogues maintaining biological activity. There are established truncated 5'-epi-derivatives of muraymycin nucleoside antibiotics with reported antibacterial properties, but the lengthy preparation of such compounds is a major

  核苷类抗生素代表了一类有前途的天然产物，可用于开发新型抗菌剂，特别是在结构简化的类似物保持生物活性方面。已经建立了具有抗菌特性的 muraymycin 核苷抗生素的截短 5'-epi-衍生物，但此类化合物的冗长制备是更详细的构效关系 (SAR) 研究的主要障碍。本文报道了基于先前报道的使用硫叶立德化学方法对截短的 5'-epi-muraymycins 进行简明、改进的合成。这种策略的高度收敛性将允许有效合成新型 muraymycin 类似物以进行彻底的 SAR 研究。
• Antibiotic AA 896 analogs
  申请人：American Cyanamid Company

  公开号：US20030087874A1

  公开（公告）日：2003-05-08

  The invention provides compounds of the Formula 1 1 wherein the definitions of m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are in the specification. These compounds are useful as antibacterial agents.

  本发明提供了式子11的化合物，其中m、n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12和R13的定义在规范中。这些化合物可用作抗菌剂。
• Silicon-mediated reductive coupling of aldehydes and allylic alcohols. A stereoselective synthesis of tunicaminyluracil
  作者：Andrew G. Myers、David Y. Gin、Katherine L. Widdowson

  DOI：10.1021/ja00025a036

  日期：1991.12
• Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V
  作者：Andrew G. Myers、David Y. Gin、Daniel H. Rogers

  DOI：10.1021/ja00090a018

  日期：1994.6

  A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.