(i-Pr2N)2POC(CH3)2CH2CN | 103930-70-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (i-Pr2N)2POC(CH3)2CH2CN
• 英文别名: 3-Bis[di(propan-2-yl)amino]phosphanyloxy-3-methylbutanenitrile；3-bis[di(propan-2-yl)amino]phosphanyloxy-3-methylbutanenitrile
• CAS: 103930-70-7
• 化学式: C₁₇H₃₆N₃OP
• 分子量: 329.466
• InChiKey: UOOJYQBGNXKNTM-UHFFFAOYSA-N

物化性质

• 沸点：
  392.3±44.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (i-Pr2N)2POC(CH3)2CH2CN 、 保护胸苷 以 乙腈 为溶剂， 反应 24.0h， 以100%的产率得到1,1-dimethyl-2-cyanoethyl 5'-O-(4,4'-dimethoxytrityl)thymidin-3'-yl N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  Sulfurization of Dinucleoside Phosphite Triesters with Chiral Disulfides

  摘要：

  Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a beta-cyanoethoxy or siloxy group. Each mixture of S-p:R-p, phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the R-ps:S-ps diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for R-ps and S-ps phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.

  DOI：

  10.1080/15257770.2011.597366
• 作为产物：
  描述：

  3-羟基-3-甲基丁腈 、 双二异丙基氨基氯化磷 在 1-methyl-3H-imidazolium trifluoromethylsulfonate 作用下， 以90%的产率得到(i-Pr2N)2POC(CH3)2CH2CN
  参考文献：
  名称：

  Sulfurization of Dinucleoside Phosphite Triesters with Chiral Disulfides

  摘要：

  Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a beta-cyanoethoxy or siloxy group. Each mixture of S-p:R-p, phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the R-ps:S-ps diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for R-ps and S-ps phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.

  DOI：

  10.1080/15257770.2011.597366

文献信息

• [EN] EXOCYLIC NITROGEN ATOM PROTECTED NUCLOSIDE AND METHOD FOR PRODUCING AND USING THE SAME<br/>[FR] NUCLÉOSIDE À ATOME D'AZOTE EXOCYCLIQUE PROTÉGÉ ET PROCÉDÉ POUR LE PRODUIRE ET L'UTILISER
  申请人：UNIV COLORADO REGENTS

  公开号：WO2014022839A1

  公开（公告）日：2014-02-06

  The present invention provides nucleosides comprising a sterically hindered silyl protecting group on the exocyclic nitrogen atom of the nucleobase, oligonucleotides comprising the same, and methods for producing the same. In particular, the silyl protecting group is a sufficiently sterically hindered such that it is stable to a various oligonucleotide synthesis procedures.

  本发明提供了包含核碱基外环氮原子上的立体阻碍硅保护基的核苷，包括相同的寡核苷酸，并提供了制备这些核苷的方法。特别地，硅保护基足够立体阻碍以使其在各种寡核苷酸合成过程中稳定。
• Exocyclic nitrogen atom protected nucleoside and method for producing and using the same
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US10414790B2

  公开（公告）日：2019-09-17

  The present invention provides nucleosides an exocyclic amine-protected nucleoside of the formula: A-B where A is a 5′-protected ribose, 5′-protected-2-deoxyribose, 5′-protected-3′-phosphoramidite ribose, or 5′-protected-3′-phosphoramidite-2-deoxyribose moiety; and B is a nucleobase having an exocyclic amine group that is protected with di-tert-butylisobutylsilyl (“BIBS”) protecting group. Use of BIBS protecting group provides an exocyclic amine-protected nucleoside that is stable to a wide variety of reaction conditions associated with oligonucleotide synthesis. The present invention also provides, oligonucleotides comprising the same, and methods for producing the same.

  本发明提供了式中的外环胺保护核苷：其中 A 是 5′保护的核糖、5′保护的-2-脱氧核糖、5′保护的-3′-亚磷酰胺核糖或 5′保护的-3′-亚磷酰胺-2-脱氧核糖分子；B 是具有外环胺基团的核碱基，该基团受二叔丁基异丁基硅烷（"BIBS"）保护基团的保护。使用 BIBS 保护基团可提供一种外环胺保护核苷，它对与寡核苷酸合成相关的各种反应条件都很稳定。本发明还提供了包含这种核苷酸的寡核苷酸以及生产这种核苷酸的方法。
• EXOCYLIC NITROGEN ATOM PROTECTED NUCLEOSIDE AND METHOD FOR PRODUCING AND USING THE SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE

  公开号：US20150225442A1

  公开（公告）日：2015-08-13

  The present invention provides nucleosides comprising a sterically hindered silyl protecting group on the exocyclic nitrogen atom of the nucleobase, oligonucleotides comprising the same, and methods for producing the same. In particular, the silyl protecting group is a sufficiently sterically hindered such that it is stable to a various oligonucleotide synthesis procedures.
• Sulfurization of Dinucleoside Phosphite Triesters with Chiral Disulfides
  作者：Joshua A. Mukhlall、William H. Hersh

  DOI：10.1080/15257770.2011.597366

  日期：2011.9

  Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a beta-cyanoethoxy or siloxy group. Each mixture of S-p:R-p, phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the R-ps:S-ps diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for R-ps and S-ps phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.