(2R,3S,5R,6R)-(3R,4S,E)-4-hydroxy-6-iodo-4-methylhex-5-en-3-yl 3,6-bis((tert-butyldimethylsilyl)oxy)-5-methoxy-2,6-dimethyl-9-oxononanoate | 1330118-84-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,5R,6R)-(3R,4S,E)-4-hydroxy-6-iodo-4-methylhex-5-en-3-yl 3,6-bis((tert-butyldimethylsilyl)oxy)-5-methoxy-2,6-dimethyl-9-oxononanoate
• 英文别名: [(E,3R,4S)-4-hydroxy-6-iodo-4-methylhex-5-en-3-yl] (2R,3S,5R,6R)-3,6-bis[[tert-butyl(dimethyl)silyl]oxy]-5-methoxy-2,6-dimethyl-9-oxononanoate
• CAS: 1330118-84-7
• 化学式: C₃₁H₆₁IO₇Si₂
• 分子量: 728.897
• InChiKey: CJSZCFPNTSSLQX-YNMWXLFPSA-N

物化性质

• 沸点：
  622.4±55.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R,6R)-(3R,4S,E)-4-hydroxy-6-iodo-4-methylhex-5-en-3-yl 3,6-bis((tert-butyldimethylsilyl)oxy)-5-methoxy-2,6-dimethyl-9-oxononanoate 在 chromium dichloride 、 nickel dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以50%的产率得到(3R,4S,6R,7R,13S,14R,E)-4,7-bis((tert-butyldimethylsilyl)-oxy)-14-ethyl-10,13-dihydroxy-6-methoxy-3,7,13-trimethyloxacyclotetradec-11-en-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (-)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.

  DOI：

  10.1021/jo201319b
• 作为产物：
  描述：

  ((4S,5R)-5-ethyl-2,2,4-trimethyl-1,3-dioxolan-4-yl)methanol 在 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 偶氮二异丁腈 、 camphor-10-sulfonic acid 、 水 、 三正丁基氢锡 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 18.0h， 生成 (2R,3S,5R,6R)-(3R,4S,E)-4-hydroxy-6-iodo-4-methylhex-5-en-3-yl 3,6-bis((tert-butyldimethylsilyl)oxy)-5-methoxy-2,6-dimethyl-9-oxononanoate
  参考文献：
  名称：

  Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (-)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.

  DOI：

  10.1021/jo201319b