(2S,6R)-2-acetoxymethyl-6-hydroxymethylpiperidine-1-carboxylic acid benzyl ester | 251983-85-4

• 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: (2S,6R)-2-acetoxymethyl-6-hydroxymethylpiperidine-1-carboxylic acid benzyl ester
• 英文别名: N-benzyloxycarbonyl-cis-2(S)-(acetoxymethyl)-6(R)-(hydroxymethyl)piperidine；benzyl (2S,6R)-2-(acetoxymethyl)-6-(hydroxymethyl)piperidine-1-carboxylate；benzyl (2S,6R)-2-(acetyloxymethyl)-6-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 251983-85-4
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: BCBKYCKCENNWQG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2-acetoxymethyl-6-hydroxymethylpiperidine-1-carboxylic acid benzyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， 反应 43.25h， 生成 methyl (8aS)-3-oxo-5-(phenylthio)hexahydro-1H-oxazolo[3,4-a]pyridine-5-carboxylate
  参考文献：
  名称：

  Formal Synthesis of Gephyrotoxin 287C

  摘要：

  DOI：

  10.3987/com-18-s(f)25
• 作为产物：
  描述：

  乙酸乙烯酯 、 N-carbobenzoxy-cis-2,6-bis(hydroxymethyl)piperidine 在 lipase from Candida cylindracea 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 24.0h， 以90%的产率得到(2S,6R)-2-acetoxymethyl-6-hydroxymethylpiperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  A chemoenzymatic-RCM strategy for the enantioselective synthesis of new dihydroxylated 5-hydroxymethyl-indolizidines and 6-hydroxymethyl-quinolizidines

  摘要：

  A direct method for the synthesis of new azasugars-like compounds has been developed, which involves a new biocatalytic protocol based on the use of a lipase from Candida Cylindracea and of a ionic liquid as reaction medium, to prepare the key Cl-symmetric piperidine precursor. By subsequent application of RCM reactions and OSO4-catalyzed double bond syn-dihydroxylation, the synthesis of the target compounds could be accomplished in a straightforward and stereocontrolled manner. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.07.017

文献信息

• Synthesis of (+)-Methyl Dihydropalustramate and of the Pyrido[1,2-a]azepine Core of Stemona Alkaloids
  作者：Thorsten Bach、Camilla Mayer、Alexandra Romek

  DOI：10.1055/s-0034-1380685

  日期：——

  Starting from a readily available, enantiomerically pure 2,6-disubstituted piperidine the synthesis of pyrido[1,2-a]azepines was accomplished. Key reactions for the ring closure were a photochemically induced acyl radical addition or a SmI2-promoted ketyl radical addition to an α,β-unsaturated ester. En route to the cyclization precursor an epoxidiation/ring opening sequence led to an undesired oxazolidinone

  从容易获得的对映体纯的 2,6-二取代哌啶开始，完成了吡啶并 [1,2-a] 氮杂环庚烷的合成。闭环的关键反应是光化学诱导的酰基自由基加成或 SmI2 促进的羰基自由基加成到 α,β-不饱和酯。在环化前体的途中，环氧化/开环序列导致不想要的恶唑烷酮，结果证明它对配置分配有用。该化合物成功转化为(+)-甲基二氢palustramate。
• Enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D
  作者：Robert Chênevert、Ghodsi Mohammadi Ziarani、Marie Pascale Morin、Mohammed Dasser

  DOI：10.1016/s0957-4166(99)00315-8

  日期：1999.8

  The stereoselective acylation of meso piperidines 3a,b by vinyl acetate (solvent and acyl donor) in the presence of Candida antarctica lipase gave the corresponding (2S,6R) and (2S,4R,6R) monoesters 2a,b in high enantiomeric purity. (5S,9S)-(+)-Indolizidine 209D was prepared in eight steps from (2S,6R)-2a. (C) 1999 Elsevier Science Ltd. All rights reserved.