(3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidine

• 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,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidine
• 英文别名: (3R,4S,5S)-3.4-dihydroxy-5-(hydroxymethyl)piperidine；(3R,4S,5S)-5-hydroxymethyl-3,4-dihydroxypiperidine；(3R,4S,5S)-5-(hydroxymethyl)piperidin-3,4-diol；5-(hydroxymethyl)piperidine-3,4-diol；L-allo-isofagomine；(-)-3-epi-isofagomine；(3R,4S,5S)-5-(hydroxymethyl)piperidine-3,4-diol
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: QPYJXFZUIJOGNX-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 Pd/C 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到(3R,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)piperidine
  参考文献：
  名称：

  来自2- C-甲基糖内酯的羟基化的C-支化的吡咯烷，C-支化的脯氨酸和C-支化的哌啶；三氟甲磺酸的有效叠氮化物位移与构型反转

  摘要：

  3,4-的通用性Ô异亚丙基-2- Ç甲基- d-arabinonolactone [从d-erythronolactone]作为Chiron公司复杂哌啶和吡咯烷是通过合成出（2R，3S，4S） -和（ 2R，3S，4R）-二羟基-2- C-甲基脯氨酸，1,4-二脱氧-1,4-亚氨基-4- C-甲基-1-核糖醇和1,4-二脱氧-1,4-亚氨基-脯氨酸4 - C -1-甲基-1-阿拉伯糖醇和异黄酮衍生物；对映体系列同样可从1-赤藓内酯获得。

  DOI：

  10.1016/j.tetlet.2008.09.069

文献信息

• Synthesis of l-3-epi-isofagomine, its homo-, n-butyl and bicyclic analogues from d-glucose as glycosidase inhibitors
  作者：Asadulla Mallick、A.P. John Pal、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2013.09.102

  日期：2013.11

  l-3-epi-isofagomine, its homo-, n-butyl derivatives and its bicyclic analogue as potent glycosidase inhibitor has been achieved from readily available d-glucose. Inhibition of some commercially available glycosidases was also carried out with the newly synthesized inhibitors which showed reasonably good inhibitions (9.4–198.2 μM). One of them (compound 11) showed selective inhibition of β-galactosidase.

  L-3-合成外延-isofagomine，其均聚物，Ñ丁基衍生物和其类似物双环作为有效的糖苷酶抑制剂已经从容易得到的d-葡萄糖实现的。还使用新合成的抑制剂对某些市售的糖苷酶进行了抑制，这些抑制剂表现出良好的抑制作用（9.4–198.2μM）。其中之一（化合物11）显示出对β-半乳糖苷酶的选择性抑制作用。
• Acceleration Effect of an Allylic Hydroxy Group on Ring-Closing Enyne Metathesis of Terminal Alkynes: Scope, Application, and Mechanistic Insights
  作者：Tatsushi Imahori、Hidetomo Ojima、Yuichi Yoshimura、Hiroki Takahata

  DOI：10.1002/chem.200801439

  日期：——

  acceleration effect of an allylic hydroxy group on ring-closing enyne metathesis has been found. Ring-closing enyne metathesis of terminal alkynes possessing an allylic hydroxy group proceeded smoothly without the ethylene atmosphere generally necessary to promote the reaction. The synthesis of (+)-isofagomine with the aid of this efficient reaction has been demonstrated. Mechanistic studies of the acceleration

  已经发现烯丙基羟基对闭环烯炔复分解的有趣的加速作用。具有烯丙基羟基的末端炔烃的闭环烯炔复分解反应顺利进行，而通常没有促进反应所需的乙烯气氛。已经证明了借助该有效反应的（+）-异黄花碱的合成。还进行了加速作用的机理研究。NMR研究的结果表明反应是通过“烯-然后-炔”途径进行的。动力学研究表明，由于存在烯丙基羟基，导致速率确定步骤的切换。这些结果表明，烯丙基羟基加速了Ru-卡宾物质的再进入步骤。
• Acceleration effect of allylic hydroxy group on ring-closing enyne metathesis of terminal alkynes: scope and application to the synthesis of isofagomine
  作者：Tatsushi Imahori、Hidetomo Ojima、Hiroki Tateyama、Yukiko Mihara、Hiroki Takahata

  DOI：10.1016/j.tetlet.2007.11.098

  日期：2008.1

  substituent effect on ring-closing enyne metathesis has been found. An allylic hydroxy group on enyne substrates accelerates ring-closing enyne metathesis of terminal alkynes. The reaction proceeds smoothly without ethylene atmosphere and/or more reactive newer generation Ru-carbene catalysts, which are generally necessary to promote the reaction. This efficient reaction was applied to the synthesis of

  已经发现了对闭环烯炔复分解的有趣的烯丙基取代基作用。烯炔底物上的烯丙基羟基可促进末端炔烃的闭环烯炔复分解。该反应在没有乙烯气氛和/或反应性更高的新一代Ru-卡宾催化剂的情况下顺利进行，而这通常是促进反应所必需的。将该有效反应应用于异黄酮的合成。
• Synthesis of (±)-isofagomine and its stereoisomers from arecoline
  作者：Steen Uldall Hansen、Mikael Bols

  DOI：10.1039/a909472e

  日期：——

  (±)-Isofagomine (1) and all its stereoisomers were prepared in a short synthesis from arecoline. The double bond of arecoline was isomerised to be no longer conjugated to the carboxy, and the ester reduced to (hydroxymethyl)tetrahydropyridine 5 which after dihydroxylation of the alkene, separation and N-demethylation gave 1 and its isomers.

  (±)-Isofagomine (1) 及其所有立体异构体都是由异甲氧苄啶通过简短的合成方法制备的。异构化后的异胆碱双键不再与羧基共轭，酯还原成（羟甲基）四氢吡啶 5，经过烯烃二羟基化、分离和 N-去甲基化后得到 1 及其异构体。
• 5-Trihydroxypropyl-dihydrouracil derivatives as precursors of 1-azasugars: application to the stereoselective synthesis of d-galacto-isofagomine
  作者：Pietro Spanu、Cristina de Candia、Fausta Ulgheri

  DOI：10.1016/j.tetlet.2010.02.093

  日期：2010.5

  A new route for the synthesis of isofagomine analogues has been carried out by using as precursors enantiopure 5-trihydroxypropyl-dihydrouracil derivatives obtained from aldol-type addition of 1,3-dibenzyl-dihydrouracil to isopropylidene-protected glyceraldehyde. The synthesis of d-galacto-isofagomine is reported.

  通过使用对映体纯的5-三羟丙基-二氢尿嘧啶衍生物作为前体，进行了异黄花碱类似物的合成新路线，该对映体是从1，3-二苄基-二氢尿嘧啶的醛醇型加成到异亚丙基保护的甘油醛而获得的。报道了d-半乳糖-异黄酮的合成。