tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane | 256413-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane
• 英文别名: TBDMS(-2)[Mob(-3)]D-Fuc4Me(b)-SPh；tert-butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-[(4-methoxyphenyl)methoxy]-6-methyl-2-phenylsulfanyloxan-3-yl]oxy-dimethylsilane
• CAS: 256413-34-0
• 化学式: C₂₇H₄₀O₅SSi
• 分子量: 504.763
• InChiKey: AIDSBKGSNUWLBD-CDICLKDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.52
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane 在 palladium on activated charcoal 吡啶 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 di-tert-butyl-4-methylpyridine 、 三氟甲磺酸酐 、 4 A molecular sieve 、 水 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium iodide 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.5h， 生成 (2S,3R,4S,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-[(2R,3S,4S,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-2-methyl-6-tri(propan-2-yl)silyloxyoxan-4-yl]oxy-2-(iodomethyl)-4-methyloxane-3,4-diol
  参考文献：
  名称：

  Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis

  摘要：

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.

  DOI：

  10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2R,3S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 tert-Butyl-[(2S,3R,4S,5S,6R)-5-methoxy-4-(4-methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-dimethyl-silane
  参考文献：
  名称：

  Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis

  摘要：

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.

  DOI：

  10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l

文献信息

• Total Synthesis of Everninomicin 13,384-1—Part 3: Synthesis of the DE Fragment and Completion of the Total Synthesis
  作者：K. C. Nicolaou、Helen J. Mitchell、Rosa Maria Rodríguez、Konstantina C. Fylaktakidou、Hideo Suzuki、Scott R. Conley

  DOI：10.1002/1521-3765(20000901)6:17<3149::aid-chem3149>3.0.co;2-l

  日期：2000.9.1

  The stereoselective construction of the DE fragment (2) of everninomicin 13,384-1 (1) is reported. From the two possible ways of inserting the DE fragment between the A1B(A)C and FGHA2 domains of the natural product, the sequence involving the DEFGHA2 segment was found to be the most viable. This coupling was followed by attachment of a suitably protected and activated A1B(A)C fragment which led, after orthoester construction and final deprotection to the targeted everninomicin 13,384-1 (1), completing the total synthesis of this complex naturally occurring substance.