5'-O-dimethoxytrityl-2'-O-allyluridine | 143463-62-1

• 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: 5'-O-dimethoxytrityl-2'-O-allyluridine
• 英文别名: allyl(-2)[DMT(-5)]Ribf(b)-uracil-1-yl；1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-3-prop-2-enoxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 143463-62-1
• 化学式: C₃₃H₃₄N₂O₈
• 分子量: 586.642
• InChiKey: VLYCKSOVERFURX-PMFUCWTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N,N',N'-四(1-甲基乙基)-二氨基亚磷酸 2-丙烯-1-基酯 、 5'-O-dimethoxytrityl-2'-O-allyluridine 在 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 11.0h， 以82%的产率得到1-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-prop-2-enoxyphosphanyl]oxy-3-prop-2-enoxyoxolan-2-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  A new synthetic route to oligoribonucleotides based on CpRu-catalyzed deallylation

  摘要：

  A triribonucleotide 3-5 U, which is fully protected by an allyl group at the T-hydroxy and phosphoric acid positions was synthesized, the deprotection being quantitatively achieved by use of a catalytic amount of CpRu(eta(3)-C3H5)(2-quinolinecarboxylato) in methanol. The reaction is completed within 30 min at ambient temperature. The utility of the simple allyl protecting group has the potential to open a new pathway in the synthesis of RNA-related compounds. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.032
• 作为产物：
  描述：

  N-(1-{(2R,3R,4R,5R)-3-Allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-1,2-dihydro-pyrimidin-4-yl)-2-(4-tert-butyl-phenoxy)-acetamide 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以59%的产率得到5'-O-dimethoxytrityl-2'-O-allyluridine
  参考文献：
  名称：

  Simplified synthesis of 2′-O-alkyl ribopyrimidines

  摘要：

  Direct 2'-hydroxyl alkylation (R= methyl, ethyl, propyl, pentyl or allyl) of 5'-dimethoxytrityl-N-(t-butylphenoxyacetyl or benzoyl)-cytidine 1 was achieved by reaction in the presence of silver I oxide and a catalytic amount of pyridine with excess alkyl halide. AT 0 degrees C alkylation of the 2'-hydroxyl was found to be highly selective; less than 10% dl (2'3')-O-alkylated or 3'-O-alkylated side products were detected in most cases. Quantitative deamination of 2'-O-alkylated cytidines to 2'-O-alkylated uridines were performed by refluxing in 4M aq. LiOH solution. This method simplifies access to various 2'-O-alkylated ribopyrimidines using readily available starting materials in one or two steps.

  DOI：

  10.1016/0040-4039(95)00435-f

文献信息

• [EN] EXTRAHEPATIC DELIVERY<br/>[FR] ADMINISTRATION EXTRA-HÉPATIQUE
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2021092371A3

  公开（公告）日：2021-06-17
• [EN] TRANSTHYRETIN (TTR) IRNA COMPOSITIONS AND METHODS OF USE THEREOF FOR TREATING OR PREVENTING TTR-ASSOCIATED OCULAR DISEASES<br/>[FR] COMPOSITION D'ARNI DE LA TRANSTHYRÉTINE (TTR) ET SES PROCÉDÉS D'UTILISATION POUR LE TRAITEMENT OU LA PRÉVENTION DE MALADIES OCULAIRES ASSOCIÉES À TTR
  申请人：ALNYLAM PHARMACEUTICALS INC

  公开号：WO2021092145A8

  公开（公告）日：2021-07-08
• US6090932A
  申请人：——

  公开号：US6090932A

  公开（公告）日：2000-07-18
• A new synthetic route to oligoribonucleotides based on CpRu-catalyzed deallylation
  作者：Shinji Tanaka、Takuya Hirakawa、Kazuhiro Oishi、Yoshihiro Hayakawa、Masato Kitamura

  DOI：10.1016/j.tetlet.2007.08.032

  日期：2007.10

  A triribonucleotide 3-5 U, which is fully protected by an allyl group at the T-hydroxy and phosphoric acid positions was synthesized, the deprotection being quantitatively achieved by use of a catalytic amount of CpRu(eta(3)-C3H5)(2-quinolinecarboxylato) in methanol. The reaction is completed within 30 min at ambient temperature. The utility of the simple allyl protecting group has the potential to open a new pathway in the synthesis of RNA-related compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Simplified synthesis of 2′-O-alkyl ribopyrimidines
  作者：Richard P. Hodge、Nanda D. Sinha

  DOI：10.1016/0040-4039(95)00435-f

  日期：1995.4

  Direct 2'-hydroxyl alkylation (R= methyl, ethyl, propyl, pentyl or allyl) of 5'-dimethoxytrityl-N-(t-butylphenoxyacetyl or benzoyl)-cytidine 1 was achieved by reaction in the presence of silver I oxide and a catalytic amount of pyridine with excess alkyl halide. AT 0 degrees C alkylation of the 2'-hydroxyl was found to be highly selective; less than 10% dl (2'3')-O-alkylated or 3'-O-alkylated side products were detected in most cases. Quantitative deamination of 2'-O-alkylated cytidines to 2'-O-alkylated uridines were performed by refluxing in 4M aq. LiOH solution. This method simplifies access to various 2'-O-alkylated ribopyrimidines using readily available starting materials in one or two steps.