(2R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-triethylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde | 501923-66-6

• 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,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-triethylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde
• 英文别名: (2R,4Z,6S)-4-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]-6-(triethylsilyloxymethyl)oxane-2-carbaldehyde
• CAS: 501923-66-6
• 化学式: C₃₁H₄₆O₄Si₂
• 分子量: 538.875
• InChiKey: SYUVUWGOTGVVOX-MPYYRBGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.26
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S,3S,4E,6S)-2-[1-(benzenesulfonyl)-2-methylpropan-2-yl]-6-[(2R,3R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]butyl]-4-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]-2-methoxyoxan-3-yl]oxy-triethylsilane 、 (2R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-triethylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde 在 苯基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以26%的产率得到2-(benzenesulfonyl)-3-[(2S,3S,4E,6S)-6-[(2R,3R)-2,3-bis[[tert-butyl(dimethyl)silyl]oxy]butyl]-4-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]-2-methoxy-3-triethylsilyloxyoxan-2-yl]-1-[(2R,4Z,6S)-4-[2-[tert-butyl(diphenyl)silyl]oxyethylidene]-6-(triethylsilyloxymethyl)oxan-2-yl]-3-methylbutan-1-ol
  参考文献：
  名称：

  Synthesis of a Simplified Bryostatin C-Ring Analogue That Binds to the CRD2 of Human PKC-α and Construction of a Novel BC-Analogue by an Unusual Julia Olefination Process

  摘要：

  [GRAPHICS]The synthesis of two truncated bryostatin analogues 2 and 3 is described. High-field NMR measurements on the C-ring analogue 3 in (CH3CN)-H-2 containing 25% (H2O)-H-2 have shown that it binds to the CRD2 of human PKC-alpha at virtually the same position as phorbol-13-acetate (PA) and bryostatin 1 (1). NMR titration studies have also revealed that 3 binds to the CRD2 with a potency similar in magnitude to PA but much less potently than 1.

  DOI：

  10.1021/ol027392u
• 作为产物：
  描述：

  [(2S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-2-yl]-methanol 在 2,6-二甲基吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.12h， 生成 (2R,6S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-eth-(Z)-ylidene]-6-triethylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde
  参考文献：
  名称：

  Synthesis of a Simplified Bryostatin C-Ring Analogue That Binds to the CRD2 of Human PKC-α and Construction of a Novel BC-Analogue by an Unusual Julia Olefination Process

  摘要：

  [GRAPHICS]The synthesis of two truncated bryostatin analogues 2 and 3 is described. High-field NMR measurements on the C-ring analogue 3 in (CH3CN)-H-2 containing 25% (H2O)-H-2 have shown that it binds to the CRD2 of human PKC-alpha at virtually the same position as phorbol-13-acetate (PA) and bryostatin 1 (1). NMR titration studies have also revealed that 3 binds to the CRD2 with a potency similar in magnitude to PA but much less potently than 1.

  DOI：

  10.1021/ol027392u

文献信息

• Synthesis of a Simplified Bryostatin C-Ring Analogue That Binds to the CRD2 of Human PKC-α and Construction of a Novel BC-Analogue by an Unusual Julia Olefination Process
  作者：Karl J. Hale、Mark Frigerio、Soraya Manaviazar、Marc G. Hummersone、Ian J. Fillingham、Igor G. Barsukov、Christian F. Damblon、Andreas Gescher、Gordon C. K. Roberts

  DOI：10.1021/ol027392u

  日期：2003.2.1

  [GRAPHICS]The synthesis of two truncated bryostatin analogues 2 and 3 is described. High-field NMR measurements on the C-ring analogue 3 in (CH3CN)-H-2 containing 25% (H2O)-H-2 have shown that it binds to the CRD2 of human PKC-alpha at virtually the same position as phorbol-13-acetate (PA) and bryostatin 1 (1). NMR titration studies have also revealed that 3 binds to the CRD2 with a potency similar in magnitude to PA but much less potently than 1.