(S)-2,2-dimethyl-4-hydroxy[²H₂]methyl-1,3-dioxolane | 74313-96-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2-dimethyl-4-hydroxy[²H₂]methyl-1,3-dioxolane
• 英文别名: 1,1-dideutero-((R)-2,2-dimethyl-1,3-dioxolane-yl)methanol；Isopropylidene [1-2H2]glycerol；dideuterio-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 74313-96-5
• 化学式: C₆H₁₂O₃
• 分子量: 134.144
• InChiKey: RNVYQYLELCKWAN-HNUJNQCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2,2-dimethyl-4-hydroxy[²H₂]methyl-1,3-dioxolane 在 三乙烯二胺 、 sodium t-butanolate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-[(1,1-dideuterated-1-((R)-2,2-dimethyl-1,3-dioxolane-4-yl)methyl)-1H-pyrazole-3-yl]acetamide
  参考文献：
  名称：

  一种氘代吡咯烷酮衍生物、药物组合物及其用途

  摘要：

  本发明涉及一种氘代吡咯烷酮衍生物及其制备的方法，还涉及应用其及其药物组合物治疗和预防代谢紊乱相关疾病的用途，本发明属于医药领域。

  公开号：

  CN113527265B9
• 作为产物：
  描述：

  (S)-2,2-二甲基-1,3-二氧戊环-4-甲酸 在 lithium aluminium deuteride 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2,2-dimethyl-4-hydroxy[²H₂]methyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of phospholipid-inhibitor conjugates by enzymic transphosphatidylation with phospholipase D

  摘要：

  This paper describes an efficient enzymatic procedure for the synthesis of phospholipid--inhibitor conjugates. The chemoselectivity, regioselectivity, and stereoselectivity of phospholipase-D-catalyzed phosphatidylations were investigated, and phospholipids containing inhibitors such as azasugars, nucleosides, and peptides were synthesized. These phospholipid conjugates in aqueous solution generally form liposome bilayers with multivalent inhibitors (the head groups) displayed on the surface and may find use in drug delivery and targeting. They also exhibit interesting structural features in different solvent systems as indicated in the NMR spectra.

  DOI：

  10.1021/ja00076a004

文献信息

• Fluorometabolite biosynthesis: isotopically labelled glycerol incorporations into the antibiotic nucleocidin in Streptomyces calvus
  作者：Axel Bartholomé、Jeffrey E. Janso、Usa Reilly、David O'Hagan

  DOI：10.1039/c6ob02291j

  日期：——

  Deuterium and carbon-13 labelled glycerols have been fed to Streptomyces calvus fermentations and isotope incorporation into the fluorine containing antibiotic nucleocidin have been evaluated by 19F-NMR. A single deuterium atom was incorporated from [2H5]- and (R)-[2H2]-glycerol into C-5′ of the antibiotic, suggesting that an oxidation occurs at this carbon after ribose ring assembly from glycerol

  氘和碳13标记的甘油已送入产链霉菌发酵，同位素已通过19 F-NMR评估了掺入含氟抗生素核苷的同位素。从[ 2 H 5 ]-和（R）-[ 2 H 2 ]-甘油中掺入一个氘原子到抗生素的C-5'中，这表明在甘油（戊糖）核糖环组装后，该碳上发生了氧化磷酸化途径），在核苷类生物合成过程中。
• Investigation of glycerol incorporation into soraphen A
  作者：Alison M. Hill、Jonathan P. Harris、Alexandros P. Siskos

  DOI：10.1039/a806112b

  日期：——

  Glycerol has been incorporated mid-chain into the polyketide soraphen A 1 at C-3,4 and C-11,12; the pro-(S)-hydroxymethyl group of glycerol is lost and one of the hydrogens in the pro-(R)-hydroxymethyl group is retained at C-11 which excludes hydroxymalonate as the immediate precursor to the vicinal methoxy groups at C-11,12.

  甘油已被并入聚酮化合物 soraphen A 1 的 C-3,4 和 C-11,12 的中链；甘油的原(S)-羟甲基基团丢失，原(R)-羟甲基基团中的一个氢保留在C-11处，这排除了作为C-11处邻位甲氧基基团的直接前体的羟基丙二酸,12.
• Biosynthesis of fluoroacetate and 4-fluorothreonine by Streptomyces cattleya. The stereochemical processing of glycerol
  作者：Jens Nieschalk、John T. G. Hamilton、Cormac D. Murphy、David B. Harper、David O’Hagan

  DOI：10.1039/a700498b

  日期：——

  When both (2R)-[1- 2 H 2 ]- and (2S)-[1- 2 H 2 ]-glycerol are incubated with resting cell suspensions of S. cattleya, only the 2R-enantiomer labels the fluoromethyl groups of fluoroacetate and 4-fluorothreonine, with retention of both deuterium atoms, placing metabolic and mechanistic limitations on the process of biological fluorination.

  当(2R)-[1- 2 H 2 ]-和(2S)-[1- 2 H 2 ]-甘油都与卡特兰虫的静止细胞悬浮液一起培养时，只有 2R 对映异构体能标记氟乙酸酯和 4-氟苏氨酸的氟甲基，同时保留两个氘原子，这给生物氟化过程带来了代谢和机理上的限制。
• Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine
  作者：Athanasios Papangelis、Trond Ulven

  DOI：10.1021/acs.joc.2c00335

  日期：2022.6.17

  Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without

  溶血磷脂酰胆碱 (LPC) 和磷脂酰胆碱 (PC) 是参与信号传导和免疫调节的重要膜成分。由于快速的酰基迁移，例如由色谱法诱导，LPC 的合成具有挑战性。我们在这里报告了 LPC 和混合 PC 的高度区域选择性合成，通过中间体允许特定的末端酰基引入，通过非常温和的 TBS 脱保护产生纯 LPC，无需色谱，使用 1 equiv 的 TFA 在水溶液中。该方法能够合成甘油、酰基和胆碱标记的 LPC。
• Synthesis of isotopically labelled cardiolipins
  作者：Andrzej A. Duralski、Paul J.R. Spooner、Saffron E. Rankin、Anthony Watts

  DOI：10.1016/s0040-4039(97)10829-2

  日期：1998.3

  A phosphotriester approach is used to access the complex phospholipid, cardiolipin (1) with polyunsaturated fatty acid chains. The synthetic method allows the specific incorporation of isotopic labels within the molecule and sets up the desired configuration at all three chiral centres which corresponds to the configuration of the natural phospholipid. Using such a methodology a range of pure optically active cardiolipin molecular species have been synthesized. (C) 1998 Elsevier Science Ltd. All rights reserved.