(3S,4S)-3,5-bis(benzyloxy)pentane-1,4-diol | 294188-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S)-3,5-bis(benzyloxy)pentane-1,4-diol
• 英文别名: 3,5-di-O-benzyl-2-deoxy-L-threo-pentitol；(3S,4S)-3,5-bis(phenylmethoxy)pentane-1,4-diol
• CAS: 294188-25-3
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: ZHZUBMCDANCCBT-OALUTQOASA-N

物化性质

• 沸点：
  494.5±45.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,5-bis(benzyloxy)pentane-1,4-diol 在 palladium dihydroxide 、 palladium on activated charcoal 吡啶 、 盐酸 、 ammonium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 89.5h， 生成 (2R,3S)-2-(羟甲基)吡咯烷-3-醇盐酸
  参考文献：
  名称：

  A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-Erythro-Pentitol

  摘要：

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).

  DOI：

  10.1080/07328300008544100
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 、 三氟甲磺酸 、 溴 、 肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 1.25h， 生成 (3S,4S)-3,5-bis(benzyloxy)pentane-1,4-diol
  参考文献：
  名称：

  A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-Erythro-Pentitol

  摘要：

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).

  DOI：

  10.1080/07328300008544100

文献信息

• A New DNA Building Block, 4′-Selenothymidine: Synthesis and Modification to 4′-Seleno-AZT as a Potential Anti-HIV Agent
  作者：Varughese Alexander、Won Jun Choi、Jeongha Chun、Hea Ok Kim、Ji Hye Jeon、Dilip K. Tosh、Hyuk Woo Lee、Girish Chandra、Jungwon Choi、Lak Shin Jeong

  DOI：10.1021/ol1005906

  日期：2010.5.21

  The first synthesis of 4′-selenothymidine (1), a novel DNA building block, and 4′-seleno-AZT (2) was accomplished from 2-deoxy-d-ribose via stereoselective formation of 2-deoxy-4-seleno-d-furanose 17 and a Pummerer-type base condensation as key steps. 4′-Selenothymidine (1) was discovered to adopt the same 2′-endo/3′-exo conformation as thymidine, which is unusual in that 4′-selenouridine has the opposite

  4'- selenothymidine（第一合成1），一个新的DNA构建块，和4'-硒代AZT（2）由2-脱氧-完成d -核糖经由立体选择性形成2-脱氧-4-硒的d-呋喃糖17和Pummerer型碱的缩合反应是关键步骤。发现4'-硒代嘧啶（1）具有与胸苷相同的2'-endo / 3'-exo构象，这是不寻常的，因为4'-硒代尿苷具有与尿苷相反的构象。
• A New Stereospecific Synthesis of 1,2,4-Trideoxy-1,4-Imino-D-<i>Erythro</i>-Pentitol
  作者：Birgitte Mølholm Malle、Inge Lundt、Richard H. Furneaux

  DOI：10.1080/07328300008544100

  日期：2000.1

  1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The hey steps were deoxygenation at C-2 and a stereospecific inversion of the configuration at C-4. Compound 4 inhibited alpha-D-glucosidase (K-i = 25 mu M) and beta-D-glucosidase (K-i = 80 mu M).