3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite | 302346-91-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite
• 英文别名: [(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[[di(propan-2-yl)amino]-prop-2-enoxyphosphanyl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 302346-91-4
• 化学式: C₃₉H₄₃N₄O₉P
• 分子量: 742.766
• InChiKey: KXCWASHDHFAWKH-IAPGXYRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite 在 四氮唑 、 水 作用下， 以 乙腈 为溶剂， 以66%的产率得到[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[oxido(prop-2-enoxy)phosphaniumyl]oxymethyl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases

  摘要：

  Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of alpha-2,3- and alpha-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00735-7
• 作为产物：
  描述：

  胞苷 在 咪唑 、 二异丙基铵盐四氮唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite
  参考文献：
  名称：

  Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid

  摘要：

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.

  DOI：

  10.1021/jo000646+

文献信息

• Synthesis of Anomeric Sulfur Analogues of CMP-Neu5Ac Containing Tethered Alkane or Arene
  作者：Wen-Shan Li、Kai-Hsuan Chang、Ying Shin Tao

  DOI：10.1055/s-2003-43349

  日期：——

  A new approach to the synthesis of anomeric sulfur analogues of CMP-Neu5Ac containing alkane or arene linkage 1a-d is described. The procedure involves the high β-stereoselectivity in sialylation of the peracetylated sialic acid methyl ester 4 with mercaptoalkyl (aryl) trichloroacetate 5a-d, followed by selective deprotection of the trichloroacetyl group to the corresponding hydroxyalkyl and hydroxyaryl thioglycosides 2a-d. Subsequent O-phosphitylation of 2a-d with respective 3a or 3c, followed by oxidation and deprotection led to the isolation of the target compounds 1a-d in good yields.

  本文介绍了一种合成含有烷或炔连接 1a-d 的 CMP-Neu5Ac 异构体硫类似物的新方法。该过程包括用巯基烷基（芳基）三氯乙酸 5a-d 对过乙酰化的硅酸甲酯 4 进行高δ-严格选择性的硅烷基化，然后选择性地将三氯乙酰基脱保护，得到相应的羟基烷基和羟基芳基硫代糖苷 2a-d。2a-d 与各自的 3a 或 3c 发生 O-磷酸化反应，然后进行氧化和脱保护，最终以良好的产率分离出目标化合物 1a-d。
• Synthesis and Characterization of an Anomeric Sulfur Analogue of CMP-Sialic Acid
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/jo000646+

  日期：2000.9.1

  alpha-2,3-Sialyltransferase catalyzes the transfer of sialic acid from CMP-sialic acid (1) to a lactose acceptor. An analogue of 1 was synthesized in which the anomeric oxygen atom was replaced with a sulfur atom (1S). The key step in the synthesis of 1S was a tetrazole-promoted coupling of a cytidine-5'-phosphoramidite with a glycosyl thiol of a protected sialic acid. Compounds 1 and 1S were characterized for their activity in a sialyl transfer assay. The rate of solvolysis in aqueous buffer of analogue 1S was 50-fold slower than that of 1. Analogue 1S was found to be substrate for alpha-2,3-sialyltransferase. The K-m of 1S was just 3-fold higher than that of 1, while the k(cat) of 1S was 2 orders of magnitude lower compared to 1.
• Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases
  作者：Lisa J. Whalen、Kerry A. McEvoy、Randall L. Halcomb

  DOI：10.1016/s0960-894x(02)00735-7

  日期：2003.1

  Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of alpha-2,3- and alpha-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay. (C) 2002 Elsevier Science Ltd. All rights reserved.