Diphenyl-phosphinic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(quinolin-2-ylsulfanyl)-tetrahydro-furan-2-ylmethoxymethyl ester | 221012-44-8

• 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: Diphenyl-phosphinic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(quinolin-2-ylsulfanyl)-tetrahydro-furan-2-ylmethoxymethyl ester
• CAS: 221012-44-8
• 化学式: C₃₂H₃₀N₃O₆PS
• 分子量: 615.646
• InChiKey: AUYNGTHMTLWMKL-OYKXOOMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  112.51
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Diphenyl-phosphinic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(quinolin-2-ylsulfanyl)-tetrahydro-furan-2-ylmethoxymethyl ester 在 水 、 sodium cyanoborohydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 formamide 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 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-(2'-deoxy-3'-O-mesyl-5'-O-4,4'-dimethoxytrityl-β-D-threo-pentofuranosyl)-thymine 在 N-碘代丁二酰亚胺 、 甲烷磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Diphenyl-phosphinic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(quinolin-2-ylsulfanyl)-tetrahydro-furan-2-ylmethoxymethyl ester
  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