(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-tributylstannanyl-3,4-dihydro-2H-pyran | 134176-06-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-tributylstannanyl-3,4-dihydro-2H-pyran
• 英文别名: tert-butyl-[[(2R,3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-6-tributylstannyl-3,4-dihydro-2H-pyran-4-yl]oxy]-dimethylsilane
• CAS: 134176-06-0
• 化学式: C₃₀H₆₄O₃Si₂Sn
• 分子量: 647.717
• InChiKey: XWGOOCHJBFFXQM-ZSXNYYPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.46
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-tributylstannanyl-3,4-dihydro-2H-pyran 在 盐酸 、 双(乙腈)氯化钯(II) 、 sodium cyanoborohydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 [(2R,3R,4R,6R)-6-[1,5-bis(methoxymethoxy)anthracen-2-yl]-3-[tert-butyl(dimethyl)silyl]oxy-2-methyloxan-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester

  摘要：

  A synthesis of substituted anthraquinones has been developed. Commercially available anthrarufin and 1,8-dihydroxyanthraquinone were converted to the corresponding (methoxymethoxy)anthracenes. Directed metalation followed by stannylation produced stable intermediates that were either alkylated, arylated, acylated, and/or C-glycosylated. The value of this new methodology was demonstrated by the triply convergent total synthesis of vineomycinone B2 methyl ester, a representative C-glycosylanthraquinone antibiotic.

  DOI：

  10.1021/ja00015a035

文献信息

• Total Synthesis of Antitumor Antibiotic Derhodinosylurdamycin A
  作者：Hem Raj Khatri、Hai Nguyen、James K. Dunaway、Jianglong Zhu

  DOI：10.1002/chem.201502113

  日期：2015.9.21

  The first total synthesis of derhodinosylurdamycin A, an angucycline antitumor antibiotic, has been described. The synthesis features a Hauser annulation followed by pinacol coupling to construct the tetracyclic angular aglycon, a Stille coupling of glycal stannane and tetracyclic aryliodide followed by stereoselective reduction to afford the 2‐deoxy β‐C‐arylglycoside, and a late‐stage stereoselective

  已经描述了金刚霉素抗肿瘤抗生素derhodinosylurdamycin A的第一个全合成。合成的特征是豪瑟环合，然后频哪醇偶联，以构建四环角糖苷配基；糖锡烷和四环芳基碘的斯蒂尔偶联，然后进行立体选择性还原，得到2-脱氧β-C-芳基糖苷；以及后期的立体选择性糖基化反应该合成策略应适合于化学合成具有不同2-脱氧糖亚基的derhodinosylurdamycin A类似物的化学合成，以进行结构和活性关系研究。