trans-2-methoxytetrahydrofuran-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: trans-2-methoxytetrahydrofuran-3-ol
• 英文别名: (2R,3R)-2-methoxyoxolan-3-ol
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: DDIDZOMSYGWECH-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 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：

  乙酰氯 、 trans-2-methoxytetrahydrofuran-3-ol 在 吡啶 作用下， 生成 acetic acid (2-methoxytetrahydrofuran-3-yl) ester
  参考文献：
  名称：

  Pyrimidine and nucleoside γ-esters of l-Glu-Sar: Synthesis, stability and interaction with hPEPT1

  摘要：

  The aim of the present study was to improve the synthetic pathway of bioreversible dipeptide derivatives as well as evaluate the potential of using L-Glu-Sar as a pro-moiety for delivering three newly synthesised nucleoside and pyrimidine L-Glu-Sar derivatives. L-Glu(trans-2-thymine-1-yl-tetrahydrofuran-3-yl ester)-Sar (I), L-Glu(thymine-1-yl-methyl ester)-Sar (II) and L-Glu(acyclothymidine)-Sar (III) were synthesised and in vitro stability was studied in various aqueous and biological media. Affinity to and translocation via hPEPT1 was investigated in mature Caco-2 cell monolayers, grown on permeable supports. Affinity was estimated in a competition assay, using [C-14] labelled Gly-Sar (glycylsarcosine). Translocation was measured as pHi-changes induced by the substrates using the fluorescent probe BCECF and an epifluorescence microscope setup. All dipeptide derivatives released the model drugs quantitatively by specific base-catalysed hydrolysis at pH > 6.0. II was labile in aqueous buffer solution, whereas 1 and III showed appropriate stability for oral administration. In 10% porcine intestinal homogenate, the half-lives of the dipeptide derivatives indicated limited enzyme catalyzed degradation. All compounds showed good affinity to hPEPT1, but the Compounds I and III showed not to be translocated by hPEPT1. The translocation of the L-Glu-Sar derivative of acyclovir, L-Glu(acyclovir)-Sar was also investigated and showed not to take place. Consequently, L-Glu-Sar seems to be a poor pro-moiety for hPEPT1-mediated transport. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2005.02.007
• 作为产物：
  描述：

  2,3-二氢呋喃 、 过氧乙酸 以 甲醇 为溶剂， 生成 trans-2-methoxytetrahydrofuran-3-ol
  参考文献：
  名称：

  Pyrimidine and nucleoside γ-esters of l-Glu-Sar: Synthesis, stability and interaction with hPEPT1

  摘要：

  The aim of the present study was to improve the synthetic pathway of bioreversible dipeptide derivatives as well as evaluate the potential of using L-Glu-Sar as a pro-moiety for delivering three newly synthesised nucleoside and pyrimidine L-Glu-Sar derivatives. L-Glu(trans-2-thymine-1-yl-tetrahydrofuran-3-yl ester)-Sar (I), L-Glu(thymine-1-yl-methyl ester)-Sar (II) and L-Glu(acyclothymidine)-Sar (III) were synthesised and in vitro stability was studied in various aqueous and biological media. Affinity to and translocation via hPEPT1 was investigated in mature Caco-2 cell monolayers, grown on permeable supports. Affinity was estimated in a competition assay, using [C-14] labelled Gly-Sar (glycylsarcosine). Translocation was measured as pHi-changes induced by the substrates using the fluorescent probe BCECF and an epifluorescence microscope setup. All dipeptide derivatives released the model drugs quantitatively by specific base-catalysed hydrolysis at pH > 6.0. II was labile in aqueous buffer solution, whereas 1 and III showed appropriate stability for oral administration. In 10% porcine intestinal homogenate, the half-lives of the dipeptide derivatives indicated limited enzyme catalyzed degradation. All compounds showed good affinity to hPEPT1, but the Compounds I and III showed not to be translocated by hPEPT1. The translocation of the L-Glu-Sar derivative of acyclovir, L-Glu(acyclovir)-Sar was also investigated and showed not to take place. Consequently, L-Glu-Sar seems to be a poor pro-moiety for hPEPT1-mediated transport. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2005.02.007

文献信息

• Template-directed intramolecular C-glycosidation. cation-mediated synthesis of ketooxetanes from thioglycosides
  作者：Donald Craig、V.Ranjit N. Munasinghe、Jason P. Tierney、Andrew J.P. White、David J. Williams、Christopher Williamson

  DOI：10.1016/s0040-4020(99)00959-x

  日期：1999.12

  Bicyclic ketooxetanes may be assembled using cation-mediated cyclisation reactions of thioglycosides possessing silyl enol ether-containing side-chains.

  可以使用具有含甲硅烷基烯醇醚的侧链的硫代糖苷的阳离子介导的环化反应来组装双环酮肟烷。
• Epoxidation–alcoholysis of cyclic enol ethers catalyzed by Ti(OⁱPr)₄or Venturello's peroxophosphotungstate complex
  作者：Pieter Levecque、David Gammon、Henok Hadgu Kinfe、Pierre Jacobs、Dirk De Vos、Bert Sels

  DOI：10.1039/b705244h

  日期：——

  Venturello's peroxophosphotungstate compound and Ti(OiPr)4 were successfully used as catalysts for the epoxidation–alcoholysis of various dihydropyrans and dihydrofuran using H2O2 as the oxidant. Different alcohols can be used as solvents and nucleophiles, resulting in hydroxy ether products with varying alkoxy groups. The Venturello compound can also be used as catalyst in a biphasic conversion of dihydropyran, in which long chain alcohols or fatty acids are incorporated in the hydroxy ether products with high yield and (stereo)selectivity.

  Venturello的过氧磷钨酸盐化合物和Ti(OiPr)4成功用作催化剂，催化多种二氢吡喃和二氢呋喃的环氧化–醇解反应，使用H2O2作为氧化剂。不同的醇可作为溶剂和亲核试剂，导致具有不同烷氧基团的羟基醚产品。Venturello化合物也可以作为催化剂在二氢吡喃的双相转化中使用，其中长链醇或脂肪酸以高产率和（立体）选择性融入羟基醚产品中。
• Stereoselective template-directed C-glycosidation. Synthesis of bicyclic ketooxetanes via intramolecular cyclization reactions of (2-pyridylthio)glycosidic silyl enol ethers
  作者：Donald Craig、V. Ranjit N. Munasinghe

  DOI：10.1039/c39930000901

  日期：——

  Bicyclic ketooxetanes 5a, 5b and 8 are formed with excellent stereoselectivity on treatment of (2-pyridylthio)glycosidic silyl enol ethers 1a, 1b and 2 with silver(I) trifluoromethanesulfonate.

  在用银(I)三氟甲磺酸盐处理(2-吡啶硫)糖苷硅醇醚1a、1b和2时，形成了具有优秀立体选择性的双环酮氧杂烷5a、5b和8。