2',3'-O-(methoxymethylene)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine | 97997-71-2

• 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: 2',3'-O-(methoxymethylene)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine
• 英文别名: N²-propionyl-O⁶-(diphenylcarbamoyl)-2',3'-O-(methoxymethylene)guanosine；[9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2-methoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate
• CAS: 97997-71-2
• 化学式: C₂₈H₂₈N₆O₈
• 分子量: 576.566
• InChiKey: UXVQLPUSMRWVKJ-RJDAIHHJSA-N

物化性质

• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  159.39
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-(methoxymethylene)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine 生成 5'-O-<(diisopropylamino)methoxyphosphino>-2',3'-O-(methoxymethylene)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine
  参考文献：
  名称：

  HUSS, SOPHIE;GOSSELIN, GILLES;IMBACH, JEAN-LOUIS, J. ORG. CHEM., 53,(1988) N 3, 499-506

  摘要：

  DOI：
• 作为产物：
  描述：

  O⁶-(diphenylcarbamoyl)-N²-propionylguanosine 生成 2',3'-O-(methoxymethylene)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine
  参考文献：
  名称：

  HUSS, SOPHIE;GOSSELIN, GILLES;IMBACH, JEAN-LOUIS, J. ORG. CHEM., 53,(1988) N 3, 499-506

  摘要：

  DOI：

文献信息

• Chemical Synthesis of Capped Oligoribonucleotides, m⁷G^5′pppAUG and m⁷G^5′pppAUGACC
  作者：Mitsuo Sekine、Shin-ichi Nishiyama、Takashi Kamimura、Yumi Osaki、Tsujiaki Hata

  DOI：10.1246/bcsj.58.850

  日期：1985.3

  The fully-protected pAUG (15) and pAUGACC (21) were synthesized by the phosphotriester approach where the phenylthio group was employed as the internal and 5′-terminal phosphate-protecting groups. The partially unblocked oligomers (32) and (33), obtained by alkaline treatment of (15) and (21), were condensed with a capping reagent (1a) in the presence of imidazole by activation with silver nitrate to afford the capped trimer and hexamer protected with the acid-labile protecting groups, i.e., 4,4,′4″-trimethoxytrityl (TMTr), 4-monomethoxytrityl (MMTr), tetrahydropyran-2-yl (THP), and methoxymethylene (mM) groups. The protected capped oligomers were unblocked by a dilute HCl solution to afford m7G5′ pppAUG and m7G5′ pppAUGACC, which were purified by HPLC and characterized by enzyme assays.

  采用磷酯化方法合成了完全保护的pAUG (15)和pAUGACC (21)，其中苯硫基用作内部和5′-末端磷酸保护基团。通过(15)和(21)的碱性处理获得了部分未封闭的寡聚物(32)和(33)，在咪唑存在下，用硝酸银活化，与封端试剂(1a)缩合，得到用酸不稳定保护基团保护的封端三聚体和六聚体，即4,4,′4″-三甲氧基三苯甲基(TMTr)、4-单甲氧基三苯甲基(MMTr)、四氢吡喃-2-基(THP)和甲氧基甲烯基(MM)基团。用稀盐酸溶液解除保护封端的寡聚物，得到m7G5′ pppAUG和m7G5′ pppAUGACC，通过HPLC纯化，并通过酶测定进行表征。
• Synthese chimique de nucleotides possedant des liaisons phosphodiesters 2′-5′ et 3′-5′ vicinales
  作者：Sophie Huss、Gilles Gosselin、Jean-Louis Imbach

  DOI：10.1016/s0040-4039(00)95743-5

  日期：1987.1

  Two branched trinucleotides, consisting of an adenosine linked at 3′ to a cytidine and at 2′ to a guanosine or to a 2-amino-6-phenylmercapto-purine riboside were synthesized from a common precursor.

  由共同的前体合成了两个分支的三核苷酸，它们由在3'处与胞嘧啶核苷和在2'处与鸟苷或2-氨基-6-苯基巯基嘌呤核糖核苷连接的腺苷组成。
• Synthesis of a new class of 2'-phosphorylated oligoribonucleotides capable of conversion to oligoribonucleotides
  作者：Mitsuo Sekine、Shin Iimura、Kiyotaka Furusawa

  DOI：10.1021/jo00063a055

  日期：1993.5
• Synthesis of various branched triribonucleoside diphosphates by site-specific modification of a diphenylcarbamoyl-protected guanine residue
  作者：Sophie Huss、Gilles Gosselin、Jean Louis Imbach

  DOI：10.1021/jo00238a006

  日期：1988.2
• Synthesis of branched ribonucleotides related to the mechanism of splicing of eukaryotic messenger RNA
  作者：Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1021/ja00306a046

  日期：1985.10