(3S,5S)-tert-butyl 3,5-dihydroxyhexanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,5S)-tert-butyl 3,5-dihydroxyhexanoate
• 英文别名: tert-butyl (3S,5S)-3,5-dihydroxyhexanoate
• 化学式: C₁₀H₂₀O₄
• 分子量: 204.266
• InChiKey: LYNGFYDXDPBMTF-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S)-tert-butyl 3,5-dihydroxyhexanoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 三氯化铝 、 三乙基硼 、 camphor-10-sulfonic acid 、 氢气 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 23.5h， 生成 (+/-)-methyl 8-epi nonactate
  参考文献：
  名称：

  Synthesis of the Proposed Structure of Feigrisolide C

  摘要：

  Possible structures of feigrisolide C were synthesized via ring-closing olefin metathesis reaction of a diester derivative prepared from 8-epinonactic acid, but physical characteristics of the synthetic samples did not match with those of the natural sample of feigrisolide C.

  DOI：

  10.1021/ol0500160
• 作为产物：
  描述：

  3,5-二羰基己酸叔丁酯 在 glucose dehydrogenase 、 葡萄糖 、 ketoreductase KRED-104 、 ketoreductase KRED-118 、 还原型辅酶II(NADPH)四钠盐 、 sodium hydroxide 作用下， 反应 50.5h， 生成 (3S,5S)-tert-butyl 3,5-dihydroxyhexanoate
  参考文献：
  名称：

  Enzymatic Reductions for the Regio- and Stereoselective Synthesis of Hydroxy-keto Esters and Dihydroxy Esters

  摘要：

  Ketoreductases were utilized for the stereoselective synthesis of delta-hydroxy-beta-keto esters, beta-hydroxy-delta-keto esters, and beta,delta-dihydroxy esters. Seven out of eight possible stereoisomers were obtained from the enzymatic reduction of the corresponding beta,delta-diketo ester in high enantio- and diastereomeric excess.

  DOI：

  10.1021/ol3003833

文献信息

• [Zinc-Diamine]-Catalyzed Hydrosilylation of Ketones in Methanol. New Developments and Mechanistic Insights
  作者：Virginie Bette、Andr� Mortreux、Diego Savoia、Jean-Fran�ois Carpentier

  DOI：10.1002/adsc.200404283

  日期：2005.2

  The Zn-promoted direct reduction of various ketones, including alkyl aryl ketones, α- and β-keto esters, α- and β-keto amides, into the corresponding alcohols with polymethylhydrosiloxane (PMHS) in protic conditions is reported. The reaction proceeds chemoselectively under smooth conditions, with simple catalyst combinations based on a zinc precursor [ZnEt2, Zn(OMe)2, Zn(OH)2] and a 1,2-diamine ligand

  据报道，在质子条件下，用聚甲基氢硅氧烷（PMHS）锌促进了各种酮的直接还原，包括烷基芳基酮，α-和β-酮酯，α-和β-酮酰胺，转化为相应的醇。该反应在光滑条件下以基于锌前体[ZnEt 2，Zn（OMe）2，Zn（OH）2 ]和1,2-二胺配体（例如N，N'）的简单催化剂组合在化学条件下进行化学选择-二苄基乙二胺（dbea）。反应速率明显比非质子条件快。对于β-酮酸酯和酰胺，需要使用过量的PMHS。使用多种对映纯二胺配体已经获得了中等对映选择性（ee高达55％）。在合成[（二胺）Zn（醇盐）2 ]配合物的基础上，提出了两种用于新催化反应的机理，所述配合物是可能的反应中间体的模型及其活性的研究。
• Total Synthesis of Cladosins B and C
  作者：Keith P. Reber、James Mease、Justin Kim

  DOI：10.1021/acs.joc.0c01605

  日期：2020.9.4

  A convergent synthetic route to the fungal metabolites cladosins B and C has been developed, affording these natural products in 29% and 27% overall yield, respectively. The cladosins are rare examples of hybrid polyketides featuring a 3-enamine tetramic acid group derived from l-valine. Key steps in this modular six-step sequence include a DMAP-mediated O- to C-acyl rearrangement to unite the side

  已开发出一条融合的合成途径，即真菌代谢物cladassin B和C，这些天然产物的总收率分别为29％和27％。cladinsins是杂化的聚酮化合物的稀有实例，其具有衍生自1-缬氨酸的3-烯胺四酸基团。该模块化六步序列中的关键步骤包括DMAP介导的O-至C-酰基重排，以使侧链与四酸核结合，并随后使用乙酸铵或HMDS引入胺。
• Asymmetric hydrogenation of methyl 3,5-dioxohexanoate catalyzed by ru-binap complex: a short step asymmetric synthesis of dihydro-60methyl-2-H-pyran-2-one
  作者：Liming Shao、Toshiyuki Seki、Hiroyuki Kawano、Masahiko Saburi

  DOI：10.1016/0040-4039(91)80569-r

  日期：1991.12

  Hydrogenation of methyl 3,5-dioxohexanoate 3 using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyester 9, which was then converted into unsaturated lactone 4. The pathway of the hydrogenation reaction was also investigated.
• Diastereoselective synthesis of syn-3,5-dihydroxyesters via ruthenium-catalyzed asymmetric transfer hydrogenation
  作者：Kathelyne Everaere、Nicolas Franceschini、André Mortreux、Jean-François Carpentier

  DOI：10.1016/s0040-4039(02)00310-6

  日期：2002.4

  The asymmetric transfer hydrogenation of chiral 5-hydroxy-3-ketoesters in 2-propanol using chlororuthenium(II)arene/ P-amino alcohol in situ catalyst combinations or a pre-synthesized Ru-beta-amino alcohol} true catalyst, provides syn-3,5-dihydroxyesters in high yields and up to 80% de. (C) (2)002 Elsevier Science Ltd. All rights reserved.
• Synthesis of the Proposed Structure of Feigrisolide C
  作者：Woo Han Kim、Jae Hoon Jung、Lee Taek Sung、Sang Min Lim、Eun Lee

  DOI：10.1021/ol0500160

  日期：2005.3.1

  Possible structures of feigrisolide C were synthesized via ring-closing olefin metathesis reaction of a diester derivative prepared from 8-epinonactic acid, but physical characteristics of the synthetic samples did not match with those of the natural sample of feigrisolide C.