(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-1-en-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (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-1-en-3-ol
• 英文别名: (4S)-4-[(2R,3S,5S,6R)-6-[tert-butyl(dimethyl)silyl]oxy-3-methoxy-5-methyloxan-2-yl]-2-[(2S,3S,6R)-3,6-dimethoxy-3,6-dihydro-2H-pyran-2-yl]pent-1-en-3-ol
• 化学式: C₂₅H₄₆O₇Si
• 分子量: 486.722
• InChiKey: BKFQZTHJOHSVSO-XVNOZPIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  <2α(R),3α,6β>-2-<1-(1-hydroxy)ethyl>-3,6-dimethoxy-2H-pyran 在 草酰氯 、 叔丁基锂 、 一水合肼 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.34h， 生成 (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-1-en-3-ol
  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

文献信息

• Strategies for ansamycin antibiotics. asymmetric synthesis of the C(3)–C(21) subunit of herbimycin A
  作者：Stephen F. Martin、Chris Limberakis、Laurence E. Burgess、Michael Hartmann

  DOI：10.1016/s0040-4020(98)01163-6

  日期：1999.3

  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.