S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate | 90762-77-9

• 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: S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate
• 英文别名: [9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-bis(phenylsulfanyl)phosphoryloxy-3-(oxan-2-yloxy)oxolan-2-yl]-2-(propanoylamino)purin-6-yl] N,N-diphenylcarbamate
• CAS: 90762-77-9
• 化学式: C₆₄H₆₁N₆O₁₁PS₂
• 分子量: 1185.33
• InChiKey: JWYYCQQAIFXFGY-DWLYMMNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.42
• 重原子数：
  84.0
• 可旋转键数：
  22.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  183.92
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate 在 zinc dibromide 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 0.05h， 以99%的产率得到Diphenyl-carbamic acid 9-[(2R,3R,4R,5R)-4-(bis-phenylsulfanyl-phosphoryloxy)-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-2-propionylamino-9H-purin-6-yl 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
• 作为产物：
  描述：

  3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine 在 吡啶 、 potassium fluoride 、 四乙基溴化铵 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.75h， 生成 S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate
  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。
• SEKINE, MITSUO;IWASE, REIKO;MASUDA, NARIHIRO;HATA, TSUJIAKI, BULL. CHEM. SOC. JAP., 61,(1988) N 5, 1669-1677
  作者：SEKINE, MITSUO、IWASE, REIKO、MASUDA, NARIHIRO、HATA, TSUJIAKI

  DOI：——

  日期：——