N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine | 108554-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine
• 英文别名: prop-2-enyl N-[9-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]purin-6-yl]carbamate
• CAS: 108554-88-7
• 化学式: C₃₅H₃₅N₅O₇
• 分子量: 637.692
• InChiKey: ZQZJXNBMTGCBOT-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine 在 六氟异丙醇 作用下， 反应 1.0h， 以85%的产率得到N⁶-[(allyloxy)carbonyl]-2'-deoxyadenosine
  参考文献：
  名称：

  1,1,1,3,3,3-六氟-2-丙醇，用于从酸敏感性核苷和核苷酸的5'-羟基中除去4,4'-二甲氧基trityI保护基

  摘要：

  引入1,1,1,3,3,3-六氟-2-丙醇作为合适的试剂和溶剂，用于5'- O-（4,4'-二甲氧基三苯甲基）-核苷和-deoxynucleosides，特别是那些的脱三苯胺稀释在更强的酸性条件下易受N-糖基裂解的影响。

  DOI：

  10.1016/0040-4039(95)01673-6
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 N⁶-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxyadenosine
  参考文献：
  名称：

  The allylic protection method in solid-phase oligonucleotide synthesis. An efficient preparation of solid-anchored DNA oligomers

  摘要：

  DOI：

  10.1021/ja00161a006

文献信息

• 4-Oxoheptanedioic acid: an orthogonal linker for solid-phase synthesis of base-sensitive oligonucleotides
  作者：Anna Leisvuori、Päivi Poijärvi-Virta、Pasi Virta、Harri Lönnberg

  DOI：10.1016/j.tetlet.2008.04.131

  日期：2008.6

  hydrazinium acetate treatment. To demonstrate the applicability of the procedure, nucleosides have been derivatized with this simple difunctional linker arm, anchored to a solid phase and subjected to synthesis and subsequent release of oligonucleotides bearing a base-sensitive biodegradable phosphate protection.

  已经发现在1，8-二氮杂双环[5，4，0]十一烷基-7-烯（DBU）存在下，1，6-二氧杂螺并[4，4]壬烷-2，7-二酮容易与醇反应。所获得的4-氧代庚二酸系链带有（1）能够使锚固到氨基烷基化树脂上的游离羧基，和（2）4-氧代丁酸酯结构基序，其允许通过温和的乙酸乙酰肼处理释放目标醇。为了证明该方法的适用性，已用这种简单的双功能连接臂衍生了核苷，将其锚固在固相上，进行合成并随后释放带有碱基敏感的可生物降解的磷酸盐保护的寡核苷酸。
• Phosphoramidite compounds and process for production thereof
  申请人：NIPPON ZEON CO., LTD.

  公开号：EP0216357A2

  公开（公告）日：1987-04-01

  Phosphoramidite compounds of the general formula wherein each of R, and R2 represents a hydroxyl group having a protective group, or the group -OR4, R3 represents a hydrogen atom, a hydroxyl group having a protective group, or the group -OR4, R4 represents the group X represents a secondary amino group, R5 represents an allylic residue or a protective group capable of being split off by beta-cleavage, and BAOC represents a nucleoside base residue in which the amino or imino group is protected with an allyloxycarbonyl-type residue, with the proviso that only one of R,, R2 and R3 represents the group-OR4. The compounds can be produced by reacting a nucleoside represented by the general formula wherein each of R'1 and R'2 cepresents a hydroxyl group which may have a protective group, R'3 represents a hydrogen atom, or a hydroxyl group which may have a protective group, and BAOC is as defined, with the proviso that only one of R'1, R'2 and R'3 is a hydroxyl group, with a phosphoramide compound represented by the general formula wherein X and R5 are as defined, and Y represents a secondary amino group or a halogen atom.

  通式如下的磷酰胺化合物 其中 R 和 R2 分别代表具有保护基团的羟基或基团-OR4，R3 代表氢原子、具有保护基团的羟基或基团-OR4，R4 代表基团 X 代表仲氨基，R5 代表烯丙基残基或能通过β-裂解作用分离的保护基团，BAOC 代表核苷碱基残基，其中的氨基或亚氨基用烯丙氧羰基型残基保护，但 R、R2 和 R3 中只有一个代表基团-OR4。这些化合物可通过与通式如下的核苷反应制得 其中 R'1 和 R'2 各代表一个可带有保护基团的羟基，R'3 代表氢原子或可带有保护基团的羟基，BAOC 如所定义，但 R'1、R'2 和 R'3 中只有一个是羟基。 其中 X 和 R5 如所定义，Y 代表仲氨基或卤原子。
• General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Masahiko Hayakawa、Ryoji Noyori

  DOI：10.1021/jo00109a024

  日期：1995.2

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.
• Allyl Protection in the Synthesis of Oligodeoxyribonucleotide Phosphorothioates
  作者：Yoshihiro Hayakawa、Masaaki Hirose、Ryoji Noyori

  DOI：10.1080/15257779408012156

  日期：1994.7

  Allyl and allyloxycarbonyl groups serve as useful protectors for internucleotide linkages and nucleoside bases, respectively, in the synthesis of partially or fully phosphorothioate-modified oligodeoxyribonucleotides.
• Use of Allylic Protecting Groups for the Synthesis of Base-Sensitive Prooligonucleotides
  作者：Nicolas Spinelli、Albert Meyer、Yoshihiro Hayakawa、Jean-Louis Imbach、Jean-Jacques Vasseur

  DOI：10.1002/1099-0690(20021)2002:1<49::aid-ejoc49>3.0.co;2-7

  日期：2002.1