(3R,4S,5R,6S)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydropyran-2-one | 202132-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5R,6S)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydropyran-2-one
• 英文别名: (3R,4S,5S,6S)-6-ethyl-4-hydroxy-3,5-dimethyloxan-2-one
• CAS: 202132-46-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: AICXQWPLZWOOSC-NGJRWZKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydropyran-2-one 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (5R,6S)-3-Chloro-6-ethyl-3,5-dimethyl-dihydro-pyran-2,4-dione
  参考文献：
  名称：

  Substrate Recognition and Channeling of Monomodules from the Pikromycin Polyketide Synthase

  摘要：

  The unique ability of the pikromycin (Pik) polyketide synthase to generate 12- and 14-membered ring macrolactones presents an opportunity to explore the fundamental processes underlying polyketide synthesis, specifically the mechanistic details of the chain extension process. We have overexpressed and purified PikAIII (module 5) and PikAIV (module 6) and assessed the ability of these proteins to generate tri- and tetraketide lactone products using N-acetylcysteamine-activated diketides and C-14-methylmalonyl-CoA as substrates. Comparison of the stereochemical specificities for PikAIII and PikAIV and the reported values for the DEBS modules reveals significant differences between these systems.

  DOI：

  10.1021/ja034841s
• 作为产物：
  描述：

  (Z)-3-trimethylsiloxy-2-pentene 生成 (3R,4S,5R,6S)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydropyran-2-one
  参考文献：
  名称：

  手性3-羟基丙酸酯2，3-二阳离子等效物的烯醇盐加成。β，δ-二羟基酯的对映选择性合成。

  摘要：

  概述了使用光学活性的二羰基环戊二烯基铁（乙烯基醚）BF（4）盐3和4作为对映选择性的3-羟基丙酸酯2,3-离子当量。配合物3和4可通过2的交换醚化而容易地获得，并且它们已被转化为对映体二羰基（η-环戊二烯基铁）（η（2）-1-甲氧基丙烯）BF（4）5和ent-5。通过交换醚化将络合物5转化为相应的对甲氧基苄氧基乙烯基醚络合物7。该盐与许多末端和非末端烯醇盐的缩合产生加合物，然后将其通过氧化还原促进的烷氧羰基化转化，然后进行醇脱保护，以形成光学活性的2-甲基-3-羟基-5酮酸酯。这些酮醇的1,3-还原可产生syn-1或anti-1，

  DOI：

  10.1021/jo9621940

文献信息

• Synthetic Chain Terminators Off-Load Intermediates from a Type I Polyketide Synthase
  作者：Manuela Tosin、Lorena Betancor、Elaine Stephens、W. M. Ariel Li、Jonathan B. Spencer、Peter F. Leadlay

  DOI：10.1002/cbic.200900772

  日期：2010.3.1

  To catch and off load: Intermediate species in type I modular polyketide biosynthesis were captured in vitro by small molecules that efficiently compete with the natural methylmalonyl extender units recruited for polyketide formation. The intermediates, which were directly off‐loaded from a whole polyketide synthase in action and characterised by LC‐HR‐ESI‐MS, are the first of their kind and prove

  赶上和卸载： I型模块化聚酮化合物生物合成中的中间物种是由小分子在体外捕获的，这些小分子可有效地与招募用于聚酮化合物形成的天然甲基丙二酸增量剂竞争。这些中间体是直接从整个聚酮化合物合酶上直接作用下来的，并通过LC-HR-ESI-MS进行了表征，是同类产品中的第一个，证明了小分子链终止剂是天然产物生物合成的便捷探针。
• Iterative Chain Elongation by a Pikromycin Monomodular Polyketide Synthase
  作者：Brian J. Beck、Courtney C. Aldrich、Robert A. Fecik、Kevin A. Reynolds、David H. Sherman

  DOI：10.1021/ja029974c

  日期：2003.4.1

  reacted alone, and synthesizes TKL (2) upon reaction in combination with PikAIV. Product formation remains dependent on the enzymatic decarboxylation of methylmalonyl-CoA and transfer of the acyl chain within the enzyme rather than acylation by propionyl-CoA from spontaneous decarboxylation. We propose that synthesis of TKL (1) by PikAIII involves iterative assembly of the triketide chain within a PikAIII

  Pikromycin 聚酮化合物合成酶 (Pik PKS) 产生 12 和 14 元环大环内酯的独特能力为探索聚酮化合物合成的基本过程提供了机会，特别是链延长过程的机械细节。我们已经过表达和纯化了 PikAIII 和 PikAIV，并证明了这些蛋白质使用 (14) C-甲基丙二酰辅酶 A 作为唯一底物生成三酮内酯产物的能力。Monomodular PikAIII 在单独反应时生成 TKL (1)，并在与 PikAIV 组合反应时合成 TKL (2)。产物的形成仍然依赖于甲基丙二酰辅酶 A 的酶促脱羧作用和酶内酰基链的转移，而不是通过丙酰辅酶 A 的自发脱羧作用进行酰化。
• US7807418B2
  申请人：——

  公开号：US7807418B2

  公开（公告）日：2010-10-05
• Substrate Recognition and Channeling of Monomodules from the Pikromycin Polyketide Synthase
  作者：Brian J. Beck、Courtney C. Aldrich、Robert A. Fecik、Kevin A. Reynolds、David H. Sherman

  DOI：10.1021/ja034841s

  日期：2003.10.1

  The unique ability of the pikromycin (Pik) polyketide synthase to generate 12- and 14-membered ring macrolactones presents an opportunity to explore the fundamental processes underlying polyketide synthesis, specifically the mechanistic details of the chain extension process. We have overexpressed and purified PikAIII (module 5) and PikAIV (module 6) and assessed the ability of these proteins to generate tri- and tetraketide lactone products using N-acetylcysteamine-activated diketides and C-14-methylmalonyl-CoA as substrates. Comparison of the stereochemical specificities for PikAIII and PikAIV and the reported values for the DEBS modules reveals significant differences between these systems.
• Enolate Additions to a Chiral 3-Hydroxypropionate 2,3-Dication Equivalent. Enantioselective Synthesis of β,δ-Dihydroxy Esters
  作者：W. Zhen、K.-H. Chu、M. Rosenblum

  DOI：10.1021/jo9621940

  日期：1997.5.1

  The use of optically active dicarbonyl cyclopentadienyliron(vinyl ether) BF(4) salts, 3 and 4, as enantioselective 3-hydroxypropionate 2,3-dication equivalents is outlined. Complexes 3 and 4 are readily available by exchange etherification of 2, and these have been transformed to enantiomeric dicarbonyl (eta-cyclopentadienyliron)(eta(2)-1-methoxypropene) BF(4) 5 and ent-5. Complex 5 has been converted

  概述了使用光学活性的二羰基环戊二烯基铁（乙烯基醚）BF（4）盐3和4作为对映选择性的3-羟基丙酸酯2,3-离子当量。配合物3和4可通过2的交换醚化而容易地获得，并且它们已被转化为对映体二羰基（η-环戊二烯基铁）（η（2）-1-甲氧基丙烯）BF（4）5和ent-5。通过交换醚化将络合物5转化为相应的对甲氧基苄氧基乙烯基醚络合物7。该盐与许多末端和非末端烯醇盐的缩合产生加合物，然后将其通过氧化还原促进的烷氧羰基化转化，然后进行醇脱保护，以形成光学活性的2-甲基-3-羟基-5酮酸酯。这些酮醇的1,3-还原可产生syn-1或anti-1，