N⁴-[(allyloxy)carbonyl]cytidine | 115516-59-1

• 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: N⁴-[(allyloxy)carbonyl]cytidine
• 英文别名: prop-2-enyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 115516-59-1
• 化学式: C₁₃H₁₇N₃O₇
• 分子量: 327.294
• InChiKey: UTVYCBGXTWMZOW-QCNRFFRDSA-N

物化性质

• 熔点：
  212-214 °C
• 密度：
  1.60±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N⁴-[(allyloxy)carbonyl]cytidine 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  The synthesis of allyl- and allyloxycarbonyl-protected RNA phosphoramidites. Useful reagents for solid-phase synthesis of RNAs with base-labile modifications

  摘要：

  The synthesis of allyl-and allyloxycarbonyl (AOC)-protected RNA phosphoramidites is reported. The use of allyl and AOC groups allows the chemistry of solid-phase RNA synthesis to be expanded to include base-labile modified nucleosides, such as acetylcytidine. The allyl-and AOC-protective chemistry can be further expanded for the construction of RNAs on solid supports and affinity columns. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00157-9
• 作为产物：
  描述：

  胞苷 在 N-甲基咪唑 、 甲醇 、 硫酸氢铵 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N⁴-[(allyloxy)carbonyl]cytidine
  参考文献：
  名称：

  A Convenient Way to N-Allyloxycarbonyl Protected Adenosine and Cytidine Derivatives

  摘要：

  开发了一种使用市售烯丙氧基羰基氯作为保护试剂，向腺嘧啶和胞嘧啶基上引入烯丙氧基羰基保护基的简便方法。

  DOI：

  10.1055/s-1998-1822

文献信息

• Diallyl dicarbonate. A convenient reagent for the synthesis of allyl carbamates.
  作者：G'erard Sennyey、Gérard Barcelo、Jean-Pierre Senet

  DOI：10.1016/s0040-4039(01)81059-5

  日期：1987.1

  Diallyldicarbonate was prepared and used for the amino protection of various compounds including amino acids, amino sugars and nucleosides.

  制备了碳酸二烯丙酯，并将其用于各种化合物的氨基保护，包括氨基酸，氨基糖和核苷。
• Improved Methods for the Preparation of 2′-Deoxyribonucleoside and Ribonucleoside 3′-Phosphoramidites with Allylic Protectors
  作者：Sophie B. Heidenhain、Yoshihiro Hayakawa

  DOI：10.1080/07328319908044842

  日期：1999.8

  Improved methods of preparing 2'-deoxyribonucleoside and ribonucleoside 3'-phosphoramidites with allylic protecting groups, which serve as useful building blocks, particularly for the synthesis of base-labile derivatives, are developed.
• SENNYEY, GERARD;BARCELO, GERARD;SENET, JEAN-PIERRE, TETRAHEDRON LETT., 28,(1987) N 47, 5809-5810
  作者：SENNYEY, GERARD、BARCELO, GERARD、SENET, JEAN-PIERRE

  DOI：——

  日期：——
• The synthesis of allyl- and allyloxycarbonyl-protected RNA phosphoramidites. Useful reagents for solid-phase synthesis of RNAs with base-labile modifications
  作者：Felicia M. Bogdan、Christine S. Chow

  DOI：10.1016/s0040-4039(98)00157-9

  日期：1998.4

  The synthesis of allyl-and allyloxycarbonyl (AOC)-protected RNA phosphoramidites is reported. The use of allyl and AOC groups allows the chemistry of solid-phase RNA synthesis to be expanded to include base-labile modified nucleosides, such as acetylcytidine. The allyl-and AOC-protective chemistry can be further expanded for the construction of RNAs on solid supports and affinity columns. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Convenient Way to <i>N</i>-Allyloxycarbonyl Protected Adenosine and Cytidine Derivatives
  作者：Sophie B. Heidenhain、Yoshihiro Hayakawa

  DOI：10.1055/s-1998-1822

  日期：1998.8

  A convenient method for the introduction of an allyloxycarbonyl protector to adenyl and cytosyl bases using commercially available allyloxycarbonyl chloride as the protecting reagent has been developed.

  开发了一种使用市售烯丙氧基羰基氯作为保护试剂，向腺嘧啶和胞嘧啶基上引入烯丙氧基羰基保护基的简便方法。