Thioacetic acid S-{(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-3-ylmethyl} ester | 175916-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: Thioacetic acid S-{(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-3-ylmethyl} ester
• CAS: 175916-04-8
• 化学式: C₃₇H₄₁N₅O₅SSi
• 分子量: 695.915
• InChiKey: ZGRJTLCALZPBQS-RVDHBOFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  49.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  128.46
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Thioacetic acid S-{(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-3-ylmethyl} ester 在 吡啶 、 Oxone 、 甲氧基三甲基硅烷 、 四溴化碳 、 氢氟酸 、 sodium acetate 、 caesium carbonate 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 29.67h， 生成 [(2R,3R,4R,5R)-2-[2-[[(2R,3R,4R,5R)-4-acetyloxy-5-(6-benzamidopurin-9-yl)-2-(2-bromoethyl)oxolan-3-yl]methylsulfonyl]ethyl]-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxyoxolan-3-yl]methyl benzoate
  参考文献：
  名称：

  Synthesis and Biodistribution of a Short Nonionic Oligonucleotide Analogue in Mouse with a Potential to Mimic Peptides

  摘要：

  A nonionic RNA analogue of the sequence r(U(SO2)G(SO2)A(SO2)C) has been synthesized where each bridging phosphate diester is replaced by a dimethylene sulfone unit (rSNA). The rSNA was synthesized in solution from 3',5'-bishomo-beta-ribonucleoside derivatives as building blocks. Full experimemtal procedures are provided, and the product and all synthetic inter mediates are fully characterized. The tetramer is nonionic but highly dipolar due to multiple hydrogen bonding opportunities. It is freely soluble in water only at higher pH's, permitting it to be radiolabeled by exchange of the acidic protons cr. to the sulfones with tritiated water. The tritiated molecule was administered intravenously into the tail vein (2.6 mg/kg) of mice, and its distribution was monitored over 48 h. The rSNA, was widely distributed in the biological tissues, including the brain, and excreted in both the feces and the urine. The accumulation of radioactivity was significantly higher in liver and kidney than in other tissues. Radiolabel was recovered from the urine, analyzed by HPLC, and shown to be intact oligonucleotide sulfone. This is the first bioavailability study on a short nonionic oligonucleotide analogue, a class of molecules with potential biomedical applications.

  DOI：

  10.1021/jm970538o
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 偶氮二甲酸二异丙酯 、 N-甲基-N-(三甲基硅烷基)三氟乙酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.7h， 生成 Thioacetic acid S-{(2R,3S,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-tetrahydro-furan-3-ylmethyl} ester
  参考文献：
  名称：

  具有二亚甲基砜桥的 RNA 的非离子类似物

  摘要：

  已经合成了 RNA 类似物，其中每个磷酸二酯连接基团都被二亚甲基砜单元（RNA 的砜连接的核酸类似物，或“rSNA”）取代。这些是...

  DOI：

  10.1021/ja952322m

文献信息

• Functionaleation of Nucleoside Analogs: Regiospecific Conversion of 4″-Hydroxyl Groups to Thioesters and Deoxygenation of 3′-Hydroxyl Groups
  作者：Zhen Huang、Steven A. Benner

  DOI：10.1080/07328319808003461

  日期：1998.5

  Nucleoside analogs 3a-e were conveniently functionalized by regiospecifically converting 4 "-hydroxyl groups to thioesters 4a-e (>90% yield) and reducing 3'-hydroxyl groups to give building blocks 2a-e in 85-90% yields.