N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine | 40653-96-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine
• 英文别名: 6-N-benzoyl-2',3'-O-isopropylidene-5'-O-(methanesulphonyl)adenosine；N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-mesyl adenosine；N⁶-benzoyl-O^{2'_,O3'_{-isopropylidene-O}5'}-methanesulfonyl-adenosine；N6-Benzoyl-5'-methansulfonyl-2',3'-isopropylidenadenosin；[(3aR,4R,6R,6aR)-4-(6-benzamidopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl methanesulfonate
• CAS: 40653-96-1
• 化学式: C₂₁H₂₃N₅O₇S
• 分子量: 489.509
• InChiKey: WBLIRNWIMHSQDT-KHTYJDQRSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine 在 18-冠醚-6 、 氨基磺酰氯 、 potassium tert-butylate 、 氨 、 碘 、 silver fluoride 、 三丁基氧化锡 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 57.17h， 生成 Nucleocidin
  参考文献：
  名称：

  Maguire, Anita R.; Meng, Wei-dong; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1795 - 1808

  摘要：

  DOI：
• 作为产物：
  描述：

  N⁶,N⁶-dibenzoyl-5'-O-mesyl-2',3'-O-isopropylidene adenosine 在 乙醇 、 氨 作用下， 反应 1.5h， 以88%的产率得到N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-methylsulfonyladenosine
  参考文献：
  名称：

  Synthesis of an Uncharged cAMP-Analogue

  摘要：

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.

  DOI：

  10.1080/15257779508014657

文献信息

• Ozonolysis of 6-N-benzoyl-9-(5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranosyl)adenine and related compounds
  作者：Bhalchandra V. Joshi、Colin B. Reese

  DOI：10.1016/s0040-4039(00)73866-4

  日期：1993.9

  The nucleoside 4',5'-olefins 3, 5, 7 and 9 are readily converted into the corresponding lactones 4, 6, 8 and 10, respectively, by ozonolysis in dichloromethane solution at -78-degrees-C.
• Design, synthesis, and molecular modeling studies of 5′-deoxy-5′-ureidoadenosine: 5′-ureido group as multiple hydrogen bonding donor in the active site of S-adenosylhomocysteine hydrolase
  作者：Ting Wang、Hyun Joo Lee、Dilip K. Tosh、Hea Ok Kim、Shantanu Pal、Sun Choi、Yoonji Lee、Hyung Ryong Moon、Long Xuan Zhao、Kang Man Lee、Lak Shin Jeong

  DOI：10.1016/j.bmcl.2007.06.013

  日期：2007.8

  5'-Deoxy-5'-ureidoadenosine was designed and synthesized as a potent inhibitor of S-adenosylhomocysteine hydrolase (SAH), in which 5'-ureido group acted as multiple hydrogen bonding donor in binding with active site residues of SAH in the molecular modeling study. (c) 2007 Published by Elsevier Ltd.
• [EN] POLYNUCLEOTIDE AND MEDICINAL COMPOSITION<br/>[FR] POLYNUCLÉOTIDE ET COMPOSITION MÉDICINALE<br/>[JA] ポリヌクレオチド及び医薬組成物
  申请人：NATIONAL UNIV CORPORATION TOKAI NATIONAL HIGHER EDUCATION AND RESEARCH SYSTEM

  公开号：WO2021132589A1

  公开（公告）日：2021-07-01

  本発明は、翻訳領域に修飾部位を有しながらも翻訳活性を維持しているポリヌクレオチドを提供することを課題とする。前記課題は、開始コドンから終止コドンまでの翻訳領域を含み、前記翻訳領域がｎ個のコドンを含み、前記ｎが２以上の正の整数であり、前記ｎ個のコドンが、それぞれ、１番目、２番目及び３番目のヌクレオチドを含み、前記ｎ個のコドンのうちの少なくとも２個のコドンにおける１番目のヌクレオチドが、糖部修飾ヌクレオチドである、ポリヌクレオチドによって解決することができる。
• Maguire, Anita R.; Meng, Wei-dong; Roberts, Stanley M., Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1795 - 1808
  作者：Maguire, Anita R.、Meng, Wei-dong、Roberts, Stanley M.、Willetts, Andrew J.

  DOI：——

  日期：——
• Synthesis of an Uncharged cAMP-Analogue
  作者：G. Ceulemans、F. Vandendriessche、J. Rozenski、P. Herdewijn

  DOI：10.1080/15257779508014657

  日期：1995.2

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.