4,5-dideoxy-2C-methyl-D-erythro-pentitol | 108510-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dideoxy-2C-methyl-D-erythro-pentitol
• 英文别名: (2S,3R)-2-methylpentane-1,2,3-triol
• CAS: 108510-19-6
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: AHFMIUJCBUIHCI-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dideoxy-2C-methyl-D-erythro-pentitol 在 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 三乙胺 作用下， 生成 (4R,5S) 2,2,4-trimethyl-5-ethyl-1,3-dioxolane-4-carboxaldehyde
  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：

  (2E)-2-methyl-2-penten-1-ol 在 titanium(IV) isopropylate 、 盐酸 、 叔丁基过氧化氢 、 sodium tetrahydroborate 、 molecular sieve 、 草酰氯 、 二甲基硫 、 3 A molecular sieve 、 四氯化锡 、 dimethyl L(+)-tartarate 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.58h， 生成 4,5-dideoxy-2C-methyl-D-erythro-pentitol
  参考文献：
  名称：

  Stuermer, Rainer, Liebigs Annalen der Chemie, 1991, # 4, p. 311 - 313

  摘要：

  DOI：

文献信息

• Highly stereoselective synthesis of methynolide, the aglycone of the 12-membered ring macrolide methymycin, from D-glucose
  作者：Yuji Oikawa、Tatsuyoshi Tanaka、Osamu Yonemitsu

  DOI：10.1016/s0040-4039(00)84871-6

  日期：1986.1

  A highly stereoselective and efficient synthesis of methynolide, the aglycone of 12-membered macrolide methymycin, was achieved from of C1–C8 and C9–C13 segments synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protecting groups.

  通过立体定向反应和苄基型保护基团，从D-葡萄糖合成的C1-C8和C9-C13片段中，实现了高立体选择性和高效率的甲基萘丙胺（十二元大环内酯间霉素的糖苷配基）的合成。
• Highly stereoselective total synthesis of methynolide, the aglycon of the 12-membered macrolide antibiotic methymycin. II. Kinetic acetalization and synthesis of the seco-acid.
  作者：YUJI OIKAWA、TATSUYOSHI TANAKA、TATSUO HAMADA、OSAMU YONEMITSU

  DOI：10.1248/cpb.35.2196

  日期：——

  A highly stereoselective synthesis of the seco-acid (3) of methynolide (1), the aglycon of the 12-membered macrolide methymycin was carried out, starting from D-glucose via the Wittig-Horner coupling of the two segments i (4) (C-9-C-13) and ii (5) (C-1-C-8), which were synthesized by the use of p-methoxybenzyl and p-methoxybenzylidene acetal protecting groups for hydroxy functions.

  以 D-葡萄糖为起点，通过 i (4) (C-9-C-13) 和 ii (5) (C-1-C-8)两个区段的 Wittig-Horner 偶联，对甲氧基苄基和对甲氧基亚苄基乙缩醛保护基团的羟基官能团合成了甲炔诺酮 (1) 的仲酸 (3)，这是 12 元大环内酯甲炔诺酮的缩合物，从而实现了甲炔诺酮 (1) 仲酸 (3) 的高度立体选择性合成。
• 14-MEMBERED KETOLIDES AND METHODS OF THEIR PREPARATION AND USE
  申请人：President and Fellows of Harvard College

  公开号：US20170305953A1

  公开（公告）日：2017-10-26

  Provided herein are methods of preparing new 14-membered ketolides via coupling of an eastern and western half moiety, followed by macro-cyclization, and optional functionalization. Intermediates in the synthesis of these ketolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using these ketolides are also provided.
• Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin
  作者：Venkata Velvadapu、Tapas Paul、Bharat Wagh、Ian Glassford、Charles DeBrosse、Rodrigo B. Andrade

  DOI：10.1021/jo201319b

  日期：2011.9.16

  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.
• Stuermer, Rainer, Liebigs Annalen der Chemie, 1991, # 4, p. 311 - 313
  作者：Stuermer, Rainer

  DOI：——

  日期：——