ethyl [bis-(4-docosoxyphenyl)methyl]carbamate | 1246541-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ethyl [bis-(4-docosoxyphenyl)methyl]carbamate
• 英文别名: N-Fmoc-di(4-docosoxyphenyl)methylamine；9H-fluoren-9-ylmethyl N-[bis(4-docosoxyphenyl)methyl]carbamate
• CAS: 1246541-60-5
• 化学式: C₇₂H₁₁₁NO₄
• 分子量: 1054.68
• InChiKey: ZYKBRLWMCZULSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.2
• 重原子数：
  77
• 可旋转键数：
  50
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl [bis-(4-docosoxyphenyl)methyl]carbamate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 Fmoc-Ala-NH-Dpm(C22)
  参考文献：
  名称：

  Novel diphenylmethyl-Derived Amide Protecting Group for Efficient Liquid-Phase Peptide Synthesis: AJIPHASE

  摘要：

  An efficient method for the synthesis of peptides bearing an amide at the C-terminal is described. This method involves the attachment of a C-terminal protecting group bearing long aliphatic chains, followed by the repetition of simple reaction and precipitation steps with the combined advantages of liquid-phase peptide synthesis (LPPS) and solid-phase peptide synthesis (SPPS). Using this method, a hydrophobic peptide was successfully synthesized in good yield and high purity, which cannot be obtained satisfactorily by SPPS.

  DOI：

  10.1021/ol302002g
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 在 sodium tetrahydroborate 、 甲烷磺酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 ethyl [bis-(4-docosoxyphenyl)methyl]carbamate
  参考文献：
  名称：

  Novel diphenylmethyl-Derived Amide Protecting Group for Efficient Liquid-Phase Peptide Synthesis: AJIPHASE

  摘要：

  An efficient method for the synthesis of peptides bearing an amide at the C-terminal is described. This method involves the attachment of a C-terminal protecting group bearing long aliphatic chains, followed by the repetition of simple reaction and precipitation steps with the combined advantages of liquid-phase peptide synthesis (LPPS) and solid-phase peptide synthesis (SPPS). Using this method, a hydrophobic peptide was successfully synthesized in good yield and high purity, which cannot be obtained satisfactorily by SPPS.

  DOI：

  10.1021/ol302002g

文献信息

• PRODUCTION METHOD OF OLIGONUCLEOTIDE
  申请人：HIRAI Kunihiro

  公开号：US20120296074A1

  公开（公告）日：2012-11-22

  The problem of the present invention is provision of a method of producing an n+p-mer oligonucleotide efficiently in a high yield, which includes use of, as a starting material, an n-mer oligonucleotide wherein the 3′-terminal hydroxyl group is protected, and the 5′-terminal hydroxyl group is protected by a temporary protecting group, and continuously performing, in a solution, (1) a deprotection step of the 5′-terminal hydroxyl group, (2) a 5′-terminal elongation step by the addition of a p-mer oligonucleotide wherein the 3′-position is phosphoramidited, and (3) an oxidation step or a sulfurization step of a phosphite triester moiety. It has been found that the above-mentioned problem can be solved by adding a particular cation scavenger during the deprotection step, applying a neutralization treatment after completion of the deprotection reaction, and using a particular oxidizing agent or sulfurizing agent in the oxidation step or sulfurization step.

  本发明的问题是提供一种高产率地有效生产n+p-mer寡核苷酸的方法，该方法包括使用n-mer寡核苷酸作为起始物，其中3'-端羟基被保护，而5'-端羟基被临时保护基保护，并在溶液中连续进行以下步骤：(1) 5'-端羟基去保护步骤，(2) 通过添加一个3'-位置为磷酰胺化的p-mer寡核苷酸进行5'-端伸长步骤，和(3) 磷酸酯三酯基的氧化步骤或硫化步骤。已经发现，通过在去保护步骤中添加特定的阳离子清除剂，在去保护反应完成后施加中和处理，并在氧化步骤或硫化步骤中使用特定的氧化剂或硫化剂，可以解决上述问题。
• DIPHENYLMETHANE COMPOUND
  申请人：TAKAHASHI Daisuke

  公开号：US20100249374A1

  公开（公告）日：2010-09-30

  Compounds having a diphenylmethane skeleton are superior in broad utility and stability, and are useful as a protecting reagent (anchor) of amino acid and/or peptide in the liquid phase synthesis and the like of a peptide having a C-terminal etc., which are of a carboxamide(-CONHR)-type, and in organic synthetic reaction methods (particularly peptide liquid phase synthetic methods), and may be contained in a kit for peptide liquid phase synthesis.

  具有二苯甲烷骨架的化合物在广泛的用途和稳定性方面表现优越，可用作液相合成中氨基酸和/或肽的保护试剂（锚点），例如具有C-末端等的肽的合成，其为羧酰胺（-CONHR）类型，并且在有机合成反应方法（特别是肽液相合成方法）中有用，可包含在用于肽液相合成的试剂盒中。
• Diphenylmethane compound
  申请人：Takahashi Daisuke

  公开号：US08722934B2

  公开（公告）日：2014-05-13

  Compounds having a diphenylmethane skeleton are superior in broad utility and stability, and are useful as a protecting reagent (anchor) of amino acid and/or peptide in the liquid phase synthesis and the like of a peptide having a C-terminal etc., which are of a carboxamide(-CONHR)-type, and in organic synthetic reaction methods (particularly peptide liquid phase synthetic methods), and may be contained in a kit for peptide liquid phase synthesis.

  具有二苯甲烷骨架的化合物在广泛的实用性和稳定性方面优于其他化合物，并且可用作氨基酸和/或肽的保护试剂（锚）在液相合成中的C-末端等具有羧酰胺（-CONHR）类型的肽以及有机合成反应方法（特别是肽液相合成方法）中使用，并且可以包含在肽液相合成试剂盒中。
• Method of making peptides using diphenylmethane compound
  申请人：AJINOMOTO CO., INC.

  公开号：US09169187B2

  公开（公告）日：2015-10-27

  The present invention aims to provide a compound superior in broad utility and stability, which is useful as a protecting reagent (anchor) of amino acid and/or peptide in liquid phase synthesis and the like of a peptide having a C-terminal etc., which are of a carboxamide (—CONHR)-type, an organic synthesis reaction method (particularly peptide liquid phase synthesis method) using the compound, and a kit for peptide liquid phase synthesis containing the compound, and has found that the object can be achieved by a particular compound having a diphenylmethane skeleton.

  本发明旨在提供一种具有广泛实用性和稳定性的化合物，该化合物可用作肽液相合成等具有C-末端的羧酰胺（—CONHR）类型的氨基酸和/或肽的保护试剂（锚点），以及使用该化合物的有机合成反应方法（特别是肽液相合成方法）和包含该化合物的肽液相合成试剂盒。本发明发现，通过具有二苯甲烷骨架的特定化合物可以实现该目的。
• METHOD FOR PRODUCING OLIGONUCLEOTIDE
  申请人：Ajinomoto Co., Inc.

  公开号：EP2711370A1

  公开（公告）日：2014-03-26

  The problem of the present invention is provision of a method of producing an n+p-mer oligonucleotide efficiently in a high yield, which includes use of, as a starting material, an n-mer oligonucleotide wherein the 3'-terminal hydroxyl group is protected, and the 5'-terminal hydroxyl group is protected by a temporary protecting group, and continuously performing, in a solution, (1) a deprotection step of the 5'-terminal hydroxyl group, (2) a 5'-terminal elongation step by the addition of a p-mer oligonucleotide wherein the 3'-position is phosphoramidited, and (3) an oxidation step or a sulfurization step of a phosphite triester moiety. It has been found that the above-mentioned problem can be solved by adding a particular cation scavenger during the deprotection step, applying a neutralization treatment after completion of the deprotection reaction, and using a particular oxidizing agent or sulfurizing agent in the oxidation step or sulfurization step.

  本发明的问题是提供一种高产率高效生产 n+p-mer 寡核苷酸的方法，该方法包括使用 n-mer 寡核苷酸作为起始材料，其中 3'末端羟基受到保护，5'末端羟基受到临时保护基团的保护、在溶液中连续进行以下步骤：(1) 5'末端羟基的去保护步骤；(2) 通过添加 p-聚合寡核苷酸进行 5'末端延伸步骤，其中 3'位被磷酸化；(3) 亚磷酸三酯分子的氧化步骤或硫化步骤。 研究发现，在脱保护步骤中加入特定的阳离子清除剂，在脱保护反应完成后进行中和处理，以及在氧化步骤或硫化步骤中使用特定的氧化剂或硫化剂，可以解决上述问题。