Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester | 90742-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester
• CAS: 90742-28-2
• 化学式: C₃₄H₃₆N₃O₉PS₂
• 分子量: 725.78
• InChiKey: NNCDNZFWNHLGCL-PYGDMHBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  147.44
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  3',5'-ApUp(3') 、 Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester 在 吡啶 作用下， 反应 1.5h， 以61%的产率得到
  参考文献：
  名称：

  Synthesis of a dodecaribonucleotide, GUAUCAAUAAUG, by use of "fully" protected ribonucleotide building blocks

  摘要：

  DOI：

  10.1021/ja00328a042
• 作为产物：
  描述：

  (+)-3’,5’-O-(1,1,3,3-四异丙基-1,3-二硅氧烷)胞苷 在 吡啶 、 potassium fluoride 、 四乙基溴化铵 、 水 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 吡啶 、 氯仿 、 乙腈 为溶剂， 反应 15.58h， 生成 Dithiophosphoric acid O-[(2R,3R,4R,5R)-2-hydroxymethyl-5-[4-(4-methoxy-benzoylamino)-2-oxo-2H-pyrimidin-1-yl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl] ester S,S'-diphenyl ester
  参考文献：
  名称：

  Synthesis of a dodecaribonucleotide, GUAUCAAUAAUG, by use of "fully" protected ribonucleotide building blocks

  摘要：

  DOI：

  10.1021/ja00328a042

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。