(3R,5R)-piperidine-3,4,5-triol hydrochloride | 187144-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,5R)-piperidine-3,4,5-triol hydrochloride
• 英文别名: des(hydroxymethyl)deoxymannojirimycin；(3R,5R)-piperidine-3,4,5-triol;hydrochloride
• CAS: 187144-38-3
• 化学式: C₅H₁₁NO₃*ClH
• 分子量: 169.608
• InChiKey: SUNAKFXBBOTQAO-VKKIDBQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.35
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.3
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-N-tert-butoxycarbonyl-5-(tert-butyldiphenylsilyloxy)-3-piperidene 在 盐酸 、 四氧化锇 、 N-甲基吲哚酮 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 丙酮 为溶剂， 反应 1.0h， 生成 (3R,5R)-piperidine-3,4,5-triol hydrochloride
  参考文献：
  名称：

  N -Boc -5-羟基-3-哌啶烯作为常见结构单元的多种1-氮杂糖的新途径

  摘要：

  描述了一种合成具有异头位置氮原子的各种1-氮杂双胍的新的通用方法。易于获得的手性N -Boc-5-羟基-3-哌啶3通过立体选择性环氧化和区域选择性环裂解，以高度立体可控的方式转化为异黄花碱（2），高异黄花碱（13）和5'-脱氧异黄花碱（14）。 。此外，3,4,5- trihydroxypiperidines（所有四种立体异构体的合成18 - 21）被划分为1-azasugar型葡糖苷酶抑制剂是立体选择性地从（手性）啶实现3。

  DOI：

  10.1021/jo050519j

文献信息

• A new asymmetric synthetic route to substituted piperidines
  作者：M. Somi Reddy、M. Narender、K. Rama Rao

  DOI：10.1016/j.tet.2006.10.073

  日期：2007.1

  An asymmetric synthesis of substituted piperidines has been described. β-Cyclodextrin- or oxazaborolidine-catalyzed asymmetric reduction of α-azido aryl ketones to the corresponding alcohols has been employed as the key step along with ring closing metathesis and selective dihydroxylation.

  已经描述了取代哌啶的不对称合成。β-环糊精或恶唑硼烷催化的α-叠氮基芳基酮不对称还原成相应的醇已被用作关键步骤以及闭环复分解和选择性二羟基化反应。
• A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies
  作者：Ganesh Pandey、Manmohan Kapur、M. Islam Khan、Sushama M. Gaikwad

  DOI：10.1039/b307455b

  日期：——

  A new synthetic strategy has been devised to access a variety of polyhydroxylated piperidines belonging to the azasugar class of glycosidase inhibitors. The key precursor (3aR, 7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro[1,3]dioxo[4,5-c]pyridine is obtained by photoinduced electron transfer (PET) cyclization of the corresponding α-trimethylsilylmethylamine radical cation to the tethered acetylene functionality. The new molecules have been evaluated for inhibitory properties for certain β-glycosidases and have been found to be moderate to weak inhibitors of the enzymes under study.

  一种新的合成策略被设计用于获得属于糖氨基酸酶抑制剂类的多羟基化哌啶的多样性。关键前驱体 (3aR, 7aR)-5-苄基-2,2-二甲基-7-亚烯基六氢[1,3]二氧杂[4,5-c]吡啶是通过光诱导电子转移（PET）环化反应获得的，该反应涉及相应的α-三甲基硅基甲基氨基自由基阳离子与连接的炔烃功能团。新分子的抑制特性已被评估，结果发现它们对某些β-糖苷酶的抑制作用为中等到弱。
• Preparation of iminosugars from aminopolyols <i>via</i> selective oxidation using galactose oxidase
  作者：Kathryn Yeow、Marianne B. Haarr、Jimmy Muldoon、Elaine O'Reilly

  DOI：10.1039/d2cc04989a

  日期：——

  Selective oxidation of minimally protected aminopolyols, using galactose oxidase variant F₂, affords biologically relevant iminosugars.

  使用半乳糖氧化酶F2变种，选择性氧化最小保护氨基多醇，可以得到具有生物学意义的亚胺糖。
• Unprecedented Oxidation of a Phenylglycinol-Derived 2-Pyridone:  Enantioselective Synthesis of Polyhydroxypiperidines
  作者：Mercedes Amat、Núria Llor、Marta Huguet、Elies Molins、Enrique Espinosa、Joan Bosch

  DOI：10.1021/ol016418z

  日期：2001.10.1

  [GRAPHICS]The phenylglycinol-derived 2-pyridone 1 undergoes m-CPBA oxidation steroselectively leading to the chiral nonracemic unsaturated bicyclic hydroxylactam 2, from which the enantioselective synthesis of (3R,5R)-3,4,5-trihydroxypiperidine (16) and the formal synthesis of the azasugar epiisofagomine are described. The enantioselective synthesis of (S)-N-Boc-3-hydroxypiperidine and (3R,4S)-3,4-dihydroxyplperidlne is also reported.
• Design and Development of a Common Synthetic Strategy for a Variety of 1-<i>N</i>-Iminosugars
  作者：Ganesh Pandey、Manmohan Kapur

  DOI：10.1021/ol026711e

  日期：2002.10.1

  [GRAPHICS]A new synthetic strategy has been developed for a general approach toward the synthesis of a variety of 1-N-iminosugar-type glycosidase inhibitors utilizing precursors developed by the PET-mediated cyclization of alpha-trimethylsilylmethylamine radical cation to a tethered pi-functionality.