1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-quinolin-2-ylsulfanyloxolan-2-yl]methoxymethylsulfanyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione | 221012-48-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-quinolin-2-ylsulfanyloxolan-2-yl]methoxymethylsulfanyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 221012-48-2
• 化学式: C₄₆H₅₁N₅O₈S₂Si
• 分子量: 894.157
• InChiKey: DVDUEMRUFIDKOE-LPFBKLPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-quinolin-2-ylsulfanyloxolan-2-yl]methoxymethylsulfanyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 水 、 sodium cyanoborohydride 作用下， 生成 1-[(2R,4S,5R)-5-[[(2R,3S,5R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]sulfanylmethoxymethyl]-4-sulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  A novel thiol protecting group: A 2-thioquinoline sulfide as a masked sulfhydryl moiety

  摘要：

  2-Thioquinoline sulfide was developed as a masked sulfhydryl entity. It is introduced through facile S(N)2 displacement reactions and is stable to a variety of reaction conditions including acids, bases and nucleophiles. It is readily unmasked using the mild treatment of sodium cyanoborohydride in acetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02694-x
• 作为产物：
  描述：

  1-[(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(quinolin-2-ylsulfanyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 在 咪唑 、 甲烷磺酸 、 水 、 sodium cyanoborohydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 formamide 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-[[(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-3-quinolin-2-ylsulfanyloxolan-2-yl]methoxymethylsulfanyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  A novel thiol protecting group: A 2-thioquinoline sulfide as a masked sulfhydryl moiety

  摘要：

  2-Thioquinoline sulfide was developed as a masked sulfhydryl entity. It is introduced through facile S(N)2 displacement reactions and is stable to a variety of reaction conditions including acids, bases and nucleophiles. It is readily unmasked using the mild treatment of sodium cyanoborohydride in acetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02694-x