6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one | 500208-43-5

• 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: 6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one
• 英文别名: (6S)-6-[(2S)-2-[tert-butyl(diphenyl)silyl]oxy-4-phenylmethoxybutyl]oxan-2-one
• CAS: 500208-43-5
• 化学式: C₃₂H₄₀O₄Si
• 分子量: 516.753
• InChiKey: OEVJXULACNKOBZ-NSOVKSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one 在 咪唑 、 2,6-二甲基吡啶 、 potassium osmate(VI) dihydrate 、 sodium periodate 、 四丙基高钌酸铵 、 三氟甲磺酸三甲基硅酯 、 2,4,6-三氯苯甲酰氯 、 (-)-(+)-methoxy(diisopinocampheyl)borane 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 49.91h， 生成
  参考文献：
  名称：

  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues

  摘要：

  The design, synthesis, and biological evaluation of a novel class of C13-diversified bryostatin analogues are described. An innovative and general strategy based on a Prins macrocyclization-nucleophilic trapping cascade was used to achieve late-stage diversification. In vitro analysis of selected library members revealed that modification at the C13 position of the bryostatin scaffold can be used as a diversification handle to regulate biological activity.

  DOI：

  10.1055/s-0033-1338860
• 作为产物：
  描述：

  4-苄氧基-2-丁酮 在 RuCl₂[(S)-BINAP] 咪唑 、 正丁基锂 、 氢气 、 silica gel 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -78.0~30.0 ℃ 、9.5 MPa 条件下， 反应 98.2h， 生成 6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one
  参考文献：
  名称：

  A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue

  摘要：

  [GRAPHICS]A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.

  DOI：

  10.1021/ol0272390

文献信息

• Design, Synthesis, and Biological Evaluation of a Potent, PKC Selective, B-Ring Analog of Bryostatin
  作者：Paul A. Wender、Vishal A. Verma

  DOI：10.1021/ol060457z

  日期：2006.4.1

  The first member of a new class of five-membered B-ring analogs of bryostatin has been synthesized and tested for its ability to bind and translocate protein kinase C (PKC). This synthesis extends the utility of our previously introduced macrotransacetalization strategy to the formation of five-membered dioxolane B-ring analogs. This analog exhibits potent, single-digit nanomolar affinity to PKC and selectively translocates novel PKC isozymes.
• A Concise, Selective Synthesis of the Polyketide Spacer Domain of a Potent Bryostatin Analogue
  作者：Paul A. Wender、Alexander V. W. Mayweg、Christopher L. VanDeusen

  DOI：10.1021/ol0272390

  日期：2003.2.1

  [GRAPHICS]A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.
• Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues
  作者：Paul Wender、Kelvin Billingsley

  DOI：10.1055/s-0033-1338860

  日期：——

  The design, synthesis, and biological evaluation of a novel class of C13-diversified bryostatin analogues are described. An innovative and general strategy based on a Prins macrocyclization-nucleophilic trapping cascade was used to achieve late-stage diversification. In vitro analysis of selected library members revealed that modification at the C13 position of the bryostatin scaffold can be used as a diversification handle to regulate biological activity.