tert-Butyl-{(2R,3S,5S,6R)-6-[(E)-(S)-3-((2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1-methyl-but-2-enyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-yloxy}-dimethyl-silane | 225510-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-{(2R,3S,5S,6R)-6-[(E)-(S)-3-((2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1-methyl-but-2-enyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-yloxy}-dimethyl-silane
• 英文别名: tert-butyl-[(2R,3S,5S,6R)-6-[(E,2S)-4-[(2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl]pent-3-en-2-yl]-5-methoxy-3-methyloxan-2-yl]oxy-dimethylsilane
• CAS: 225510-74-7
• 化学式: C₂₅H₄₆O₆Si
• 分子量: 470.722
• InChiKey: XMUJWAKEUCDAMR-LDXUWZLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-Butyl-{(2R,3S,5S,6R)-6-[(E)-(S)-3-((2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1-methyl-but-2-enyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-yloxy}-dimethyl-silane 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-{3-[(E)-(1R,2S,4S,5R,6S)-8-((2S,3S,6R)-3,6-Dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1,5-dihydroxy-4-methoxy-2,6-dimethyl-non-7-enyl]-2,5-dimethoxy-phenyl}-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Strategies for ansamycin antibiotics. asymmetric synthesis of the C(3)–C(21) subunit of herbimycin A

  摘要：

  The asymmetric synthesis of 25, which constitutes the C(3)-C(21) segment of the stereochemically complex ansa chain of herbimycin A (2) has been achieved. The approach features the furan-hydropyran transformations 7-->5 and 8-->6 and the fragment coupling of 5 and 6 to produce the trisubstituted alkene 4 with high stereoselectivity. Stereoselective addition of the aryl anion derived from 24, which possesses the novel BIPSOP protecting group for the primary amine function, to the lactol 22 then delivered 25 as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01163-6
• 作为产物：
  描述：

  Dithiocarbonic acid S-[(Z)-(S)-4-[(2R,3S,5S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-2-((2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl)-pent-2-enyl] ester S-methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以93%的产率得到tert-Butyl-{(2R,3S,5S,6R)-6-[(E)-(S)-3-((2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl)-1-methyl-but-2-enyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-yloxy}-dimethyl-silane
  参考文献：
  名称：

  Strategies for ansamycin antibiotics. asymmetric synthesis of the C(3)–C(21) subunit of herbimycin A

  摘要：

  The asymmetric synthesis of 25, which constitutes the C(3)-C(21) segment of the stereochemically complex ansa chain of herbimycin A (2) has been achieved. The approach features the furan-hydropyran transformations 7-->5 and 8-->6 and the fragment coupling of 5 and 6 to produce the trisubstituted alkene 4 with high stereoselectivity. Stereoselective addition of the aryl anion derived from 24, which possesses the novel BIPSOP protecting group for the primary amine function, to the lactol 22 then delivered 25 as the major product. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01163-6