2,3,4,5-tetra-O-acetyl-1-bromo-1-deoxy-1-S-ethyl-1-thio-aldehydo-D-ribose aldehydrol | 70094-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,5-tetra-O-acetyl-1-bromo-1-deoxy-1-S-ethyl-1-thio-aldehydo-D-ribose aldehydrol
• 英文别名: 2,3,4,5-tetra-O-acetyl-1-bromo-1-deoxy-1-S-ethyl-1-thio-D-ribitol；2,3,4,5-tetra-O-acetyl-1-bromo-1-S-ethyl-1-thio-D-ribitol
• CAS: 70094-86-9
• 化学式: C₁₅H₂₃BrO₈S
• 分子量: 443.313
• InChiKey: UQGNNSNMIOKWAJ-CBNXCZCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetra-O-acetyl-1-bromo-1-deoxy-1-S-ethyl-1-thio-aldehydo-D-ribose aldehydrol 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.33h， 生成 (-) 1-S-ethyl-1-thio-(uracil-1-yl)-D-ribitol
  参考文献：
  名称：

  Acyclic-sugar nucleoside analogs derived from cytosine with the d-aldopentoses, and from uracil with d-lyxose and d-ribose

  摘要：

  DOI：

  10.1016/s0008-6215(00)84880-6
• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-ribose diethyl dithioacetal 在 溴 作用下， 生成 2,3,4,5-tetra-O-acetyl-1-bromo-1-deoxy-1-S-ethyl-1-thio-aldehydo-D-ribose aldehydrol
  参考文献：
  名称：

  Acyclic-sugar nucleoside analogs derived from cytosine with the d-aldopentoses, and from uracil with d-lyxose and d-ribose

  摘要：

  DOI：

  10.1016/s0008-6215(00)84880-6

文献信息

• 5-Fluorouracil nucleoside analogs having acyclic-sugar chains derived from the four D-aldopentoses
  作者：Derek Horton、Robert A. Markovs

  DOI：10.1016/s0008-6215(00)84864-8

  日期：1980.4

  bromide (3) gave a syrupy, (1 R ,1S) mixture of protected nucleosides that afforded the corresponding tetrols, also as an amorphous mixture. The d - ribo bromide gave a 1:2 (1 R ,1 S ) mixed adduct; de-esterification produced the corresponding mixed tetrols ( 13 + 14 ) as a glass from which the (1S) isomer 13 could be obtained crystalline.

  摘要5-氟-2,4-双（三甲基甲硅烷氧基）嘧啶（1）与2,3,4,5-四-O-乙酰基-1-溴-1-S-乙基-1-硫基-d-的融合阿拉伯糖醇（2）产生59％的结晶2,3,4,5-四-O-乙酰基-1-S-乙基-1-（5-氟尿嘧啶-1-基）-1-硫代-d-葡萄糖基-戊醇[（1 R）-2,3,4,5-四-O-乙酰基-1-S-乙基-1-（5-氟尿嘧啶-1-基）-1-硫代-d-阿拉伯糖醇]（6），通过甲醇氨转化为相应的结晶的游离四醇10；X射线晶体学，手性数据和nmr光谱确定了6和10的C-1'立体化学，并显示该化合物有利于带有乙硫基的扩展构象，该构象与平面的锯齿形碳链反平行。将溴化物2的d-xylo类似物（3）与1缩合，得到一种混合物，从其中分离出35％的结晶（1S）核苷衍生物（7），并转化为结晶四氢萘；溶液中7的构象未延伸（镰刀形）。d-lyxo bromide（3）的相似序列产生了糖浆状（1 R
• Synthesis of the four 1-(1-deoxy-d-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain
  作者：Scott M. Vejcik、Derek Horton

  DOI：10.1016/j.carres.2006.12.003

  日期：2007.5

  Acetylated D-pentose diethyl dithioacetals were coupled by way of 1-bromo-1-ethylthio derivatives with 2,4-bis(trimethylsilyl)thymine to afford diastercomeric pairs of acyclic-sugar nucleoside analogues bearing a thymin-1-yl and an ethylthio group at C-1. Free-radical desulfurization by the action of tributylstannane removed the ethylthio group to afford the corresponding acetylated 1-(1-deoxy-D-pentitol-1-yl)thymines and subsequently the free title compounds in the arabino, lyxo, ribo, and xylo series. Conformations of the intermediates and products were studied in detail and the final products were evaluated for their potential as agents active against plant viruses and rice blast fungus. (c) 2006 Elsevier Ltd. All rights reserved.