(2R,3S)-2,3,4-三羟基-gamma-丁内酯2,3-环己基缩酮 | 186803-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2R,3S)-2,3,4-三羟基-gamma-丁内酯2,3-环己基缩酮
• 英文名称: (+)-2,3-O-cyclohexylidene-L-erythruronic acid
• 英文别名: 2,3-O-cyclohexylidene-L-erythruronolactone；2,3-cyclohexylidene-L-erythruronic acid；(2R,3S)-2,3,4-Trihydroxy-gamma-butyrolactone 2,3-Cyclohexyl Ketal；(3aR,6aS)-6-hydroxyspiro[6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-2,1'-cyclohexane]-4-one
• CAS: 186803-48-5
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: GHGRKHAVPBZSIH-KJFJCRTCSA-N

物化性质

• 熔点：
  93-95°C
• 溶解度：
  可溶于氯仿、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2,3,4-三羟基-gamma-丁内酯2,3-环己基缩酮 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到2R,3S-2,3-O-cyclohexylidene-butan-1,2,3,4-tetrol
  参考文献：
  名称：

  Cooperative attractive interactions in asymmetric hydrogenations with dihydroxydiphosphine Rh(I) catalysts — a competition study

  摘要：

  Studies for controlling rate and enantioselectivity of the asymmetric hydrogenation with Rh-diphosphine catalysts by cooperative attractive interactions within the framework of catalyst-substrate complexes are represented. In strong contrast to a Rh(I)[three-1,4-bis(diphenylphosphino)butane-2,3-diol] catalyst an extremely fast reaction took place applying the complex of the analogue erythro ligand. This is likely due to a strong intramolecular hydrogen bond between the vicinal HO groups impeding the hemilabile coordination of one of the hydroxy groups on the metal center during the hydrogenation. When a substrate with strong hydrogen bond acceptor properties such as (E)-methyl 3-dimethoxyphosphorylbut-2-enoate was hydrogenated even the three catalyst exhibited a fast reaction. The product was obtained in 83% ee. In contrast, when in the ligand both HO groups were replaced by MeO groups only poor conversion and 24% ee were achieved. While with the complex bearing HO groups in methanolic solution the corresponding diastereomeric catalyst substrate complexes were dominant, analogue MeO groups bearing catalyst substrate complexes could not be detected by NMR. For the latter, only the Rh(I)-solvent complex was found revealing the high importance of the additional functional groups on this equilibrium. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00071-1
• 作为产物：
  描述：

  (3aR,6R,6aR)-6-(羟基甲基)螺[6,6a-二氢-3aH-呋喃并[4,3-d][1,3]二氧杂环戊烯-2,1'-环己烷]-4-酮 在 sodium hydroxide 、 sodium periodate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以96%的产率得到(2R,3S)-2,3,4-三羟基-gamma-丁内酯2,3-环己基缩酮
  参考文献：
  名称：

  A New Synthesis of D-Ribonolactone from D-Ribose by Pyridinium Chlorochromate Oxidation

  摘要：

  2,3-O-Cyclohexylidene-D-ribonolactone 由 2,3-O-cyclohexylidene-D-ribose 直接通过氯铬酸吡啶鎓（PCC）氧化制备而成，收率为 55-60%。

  DOI：

  10.1055/s-1991-26609

文献信息

• A New Synthesis of D-Ribonolactone from D-Ribose by Pyridinium Chlorochromate Oxidation
  作者：Dashan Liu、Carol A. Caperelli

  DOI：10.1055/s-1991-26609

  日期：——

  2,3-O-Cyclohexylidene-D-ribonolactone is prepared directly from 2,3-O-cyclohexylidene-D-ribose by pyridinium chlorochromate (PCC) oxidation in 55-60% yield.

  2,3-O-Cyclohexylidene-D-ribonolactone 由 2,3-O-cyclohexylidene-D-ribose 直接通过氯铬酸吡啶鎓（PCC）氧化制备而成，收率为 55-60%。
• Identification of an Endogenous Organosulfur Metabolite by Interpretation of Mass Spectrometric Data
  作者：Qibo Zhang、Lisa A. Ford、Anne M. Evans、Douglas R. Toal

  DOI：10.1021/acs.orglett.8b00664

  日期：2018.4.6

  The chemical structure of x11564, a new endogenous organosulfur metabolite, was elucidated by de novo interpretation of mass spectrometric data. The structure was confirmed by comparison to a synthetic standard. Metabolite x11564 is structurally related to intermediates in the methionine salvage pathway.

  通过对质谱数据的从头解释来阐明一种新的内源性有机硫代谢物x11564的化学结构。通过与合成标准物比较确认了该结构。代谢物x11564在结构上与蛋氨酸抢救途径中的中间体有关。
• [EN] COMPOUNDS, REAGENTS, AND USES THEREOF<br/>[FR] COMPOSÉS, RÉACTIFS ET UTILISATIONS ASSOCIÉES
  申请人：METABOLON INC

  公开号：WO2019067699A1

  公开（公告）日：2019-04-04

  The present invention provides a compound of formula (I), formula (II), formula (III), (IV) or a salt thereof, compositions and methods of making the compound, methods and reagents for measuring the compound, and kits using the same. The use of a compound of formula (I), formula (II), formula (III), or formula (IV) for assessing or monitoring kidney function in a subject, determining predisposition to developing reduced kidney function, classifying a subject according to level of kidney function, and diagnosing or monitoring chronic kidney disease is also described.

  本发明提供了式(I)、式(II)、式(III)、(IV)或其盐的化合物，以及制备该化合物的组合物和方法，测定该化合物的方法和试剂，以及使用该化合物的工具包。还描述了使用式(I)、式(II)、式(III)或式(IV)的化合物来评估或监测受试者的肾功能，确定发展肾功能减退的易感性，根据肾功能水平对受试者进行分类，以及诊断或监测慢性肾脏疾病。
• Enantioselective synthesis of seven pyrrolizidine diols from a single precursor
  作者：A. Richard Chamberlin、John Y. L. Chung

  DOI：10.1021/jo00223a002

  日期：1985.11
• Synthesis of analogs of neplanocin A: utilization of optically active dihydroxycyclopentenones derived from carbohydrates
  作者：David R. Borcherding、Stephen A. Scholtz、Ronald T. Borchardt

  DOI：10.1021/jo00233a029

  日期：1987.11