(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate | 1159611-54-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-methyl 2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate
• 英文别名: methyl (E)-2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate；methyl (2E)-2-[(2S,6S)-2-[(E)-4-[(2R,6S)-6-[[(2S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(2S)-4-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]butyl]oxan-2-yl]methyl]-4-methylideneoxan-2-yl]-2-methylbut-3-en-2-yl]-6-[(2R,3R)-2-[tert-butyl(dimethyl)silyl]oxy-3-(phenylmethoxymethoxy)butyl]-2-methoxy-3-oxooxan-4-ylidene]acetate
• CAS: 1159611-54-7
• 化学式: C₇₈H₁₁₆O₁₄Si₃
• 分子量: 1362.03
• InChiKey: NFQMVRUAGUUQBP-FSSHLPPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.11
• 重原子数：
  95
• 可旋转键数：
  35
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (E)-methyl 2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 、 水 、 氯化铵 作用下， 以 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  The Bryostatin 1 A-Ring Acetate is Not the Critical Determinant for Antagonism of Phorbol Ester-Induced Biological Responses

  摘要：

  The contribution of the A-ring C(7) acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C(7) acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.

  DOI：

  10.1021/ol900585t
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(E)-methyl 2-((2S,6S)-6-((2R,3R)-3-(benzyloxymethoxy)-2-(tert-butyldimethylsilyloxy)butyl)-2-((E)-4-((2R,6S)-6-(((2S,4S,6R)-4-(tert-butyldimethylsilyloxy)-6-((S)-4-(tert-butyldiphenylsilyloxy)-2-(4-methoxybenzyloxy)butyl)tetrahydro-2H-pyran-2-yl)methyl)-4-methylenetetrahydro-2H-pyran-2-yl)-2-methylbut-3-en-2-yl)-2-methoxy-3-oxo-2H-pyran-4(3H,5H,6H)-ylidene)acetate
  参考文献：
  名称：

  The Bryostatin 1 A-Ring Acetate is Not the Critical Determinant for Antagonism of Phorbol Ester-Induced Biological Responses

  摘要：

  The contribution of the A-ring C(7) acetate to the function of bryostatin 1 has been investigated through synthesis and biological evaluation of an analogue incorporating this feature into the bryopyran core structure. No enhanced binding affinity for protein kinase C (PKC) was observed, relative to previously characterized analogues lacking the C(7) acetate. Functional assays showed biological responses characteristic of those induced by the phorbol ester PMA and distinctly different from those observed with bryostatin 1.

  DOI：

  10.1021/ol900585t

文献信息

• [EN] BRYOSTATIN ANALOGS AND USE THEREOF AS ANTIVIRAL AGENTS<br/>[FR] ANALOGUES DE LA BRYOSTATINE ET UTILISATION DE CEUX-CI EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV UTAH RES FOUND

  公开号：WO2016025363A1

  公开（公告）日：2016-02-18

  Described herein are tricyclic macrolactones. The macrolactones have a high binding affinity for PKC. The compounds described herein can be used in a number of therapeutic applications including the treatment or prevention of viral infection. Also described herein are methods for producing macrolactones. The methods permit the high-yield synthesis of macrolactones in a low number of steps and with a high degree of substitution and specificity.

  本文描述了三环大环内酯。这些大环内酯对蛋白激酶C（PKC）具有很高的结合亲和力。本文描述的化合物可用于多种治疗应用，包括治疗或预防病毒感染。本文还描述了生产大环内酯的方法。这些方法允许在较少的步骤中高产量地合成大环内酯，并具有高度的取代和特异性。
• [EN] BRYOSTATIN ANALOGUES AND METHODS OF MAKING AND USING THEREOF<br/>[FR] COMPOSÉS MACROCYCLIQUES ET PROCÉDÉS DE FABRICATION ET D'UTILISATION DE CEUX-CI
  申请人：UNIV UTAH RES FOUND

  公开号：WO2009129361A3

  公开（公告）日：2010-07-08