ethyl 2-methyl-5-[4-O-(4-methylphenylsulfonyl)-D-arabino-tetritol-1-yl]furan-3-carboxylate | 385766-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-methyl-5-[4-O-(4-methylphenylsulfonyl)-D-arabino-tetritol-1-yl]furan-3-carboxylate
• 英文别名: ethyl 2-methyl-5-[(1S,2R,3R)-1,2,3-trihydroxy-4-(4-methylphenyl)sulfonyloxybutyl]furan-3-carboxylate
• CAS: 385766-38-1
• 化学式: C₁₉H₂₄O₉S
• 分子量: 428.46
• InChiKey: SZFSVHXCMDNKMX-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  152
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-[4-O-(4-methylphenylsulfonyl)-D-arabino-tetritol-1-yl]furan-3-carboxylate 在 三氟乙酸 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 2-methyl-5-(4-thio-β-D-erythrofuranosyl)furan-3-carboxylate
  参考文献：
  名称：

  Synthesis of furan 4′-thio-C-nucleosides, their methylsulfonium and sulfoxide derivatives. Evaluation as glycosidase inhibitors

  摘要：

  A series of furan C-nucleosides having a sulfur atom in the sugar ring were synthesised. The alpha and beta anomers of 3-ethoxycarbonyl-2-methyl-5-(4'-thin-D-erythrofuranosyl)furans 10 and 11 were obtained by acid treatment of (4'-S-acetyl-4'-thin-D-arabino-tetritol-1-yl)furan 9. Oxidation of 10 with m-chloroperbenzoic acid gave sulfoxide 12 as one epimer at the sulfur atom whereas 11 was transformed into sulfoxide 13 as an epimeric mixture. S-Methylation of 10 and 11 with methyl triflate led to sulfonium salts 14 and 15. The prepared compounds were found to be moderate inhibitors of alpha-L-fucosidase. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00339-9
• 作为产物：
  描述：

  对甲苯磺酰氯 、 ethyl 2-methyl-5-(D-arabino-tetritol-1-yl)furan-3-carboxylate 以 吡啶 为溶剂， 反应 2.0h， 以57%的产率得到ethyl 2-methyl-5-[4-O-(4-methylphenylsulfonyl)-D-arabino-tetritol-1-yl]furan-3-carboxylate
  参考文献：
  名称：

  5-（1'，4'-Dideoxy-1'，4'-亚氨基-D-赤藓糖基）-2-甲基-3-糠酸（= 5-[（3 S，4 R） -3,4-二羟基吡咯烷基-2-基] -2-甲基呋喃-3-羧酸）衍生物：作为选择性α -L-岩藻糖苷酶和β-半乳糖苷酶抑制剂的新产品

  摘要：

  D-葡萄糖与乙酰乙酸乙酯的García-González反应生成5-[（1 'S）-D-赤藓糖基] -2-甲基-3-糠酸乙酯（5），然后将其转化为5-[（1' R）-1'，4'-二脱氧-1'，4'-亚氨基-D-赤藓基] -2-甲基-3-糠酸酯（3c）和乙基5-[（1 'S）-1'，4 ′-二脱氧-1′，4′-亚氨基-D-赤藓糖基] -2-甲基-3-糠酸酯（4c）。开发了类似的方法来生成其他羧酸衍生物，例如甲基（参见3e和4e），异丙基（参见3f）和丁酯（参见3g），S-苯基（参见3a）和S-乙基硫酯（请参见3m），N-苄基甲酰胺3b和4b，甘氨酸衍生的酰胺3h和N-苯基（请参见3i），N-异丙基（请参见3j和4j），N，N-二乙基-（请参见3k和4k）和N-乙基羧酰胺（参见3l）。所有新的5-（1'，4'-dideoxy-1'，4'-亚氨基-D-赤藓糖基）-3-糠酸（= 5-[（3 S，4

  DOI：

  10.1002/hlca.200390152

文献信息

• Solution and solid phase synthesis of hetarylene-carbopeptoids. A new type of peptidomimetics
  作者：A.J Moreno-Vargas、J.G Fernández-Bolaños、J Fuentes、I Robina

  DOI：10.1016/s0040-4039(00)02266-8

  日期：2001.2

  Ready access to a new class of peptidomimetics has been demonstrated by the synthesis of hetarylene-carbopeptoids using a hydroxyalkylfuran-aminoacid 7 as a novel scaffold.

  通过使用羟烷基呋喃-氨基酸7作为新型支架合成亚戊二烯-类肽类化合物，已经证明可以容易地获得一类新型的拟肽。
• New leads for selective inhibitors of α-l-fucosidases. Synthesis and glycosidase inhibitory activities of [(2R,3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]furan derivatives
  作者：Inmaculada Robina、Antonio J. Moreno-Vargas、José G. Fernández-Bolaños、José Fuentes、Raynald Demange、Pierre Vogel

  DOI：10.1016/s0960-894x(01)00497-8

  日期：2001.9

  Readily derived from D-glucose, 5-[(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-methyl-3-furoic esters and amides are selective and competitive inhibitors (K(i)> or = 3 microM) of alpha-L-fucosidase from bovine epididymis and from human placenta.

  5-[（2R，3S，4R）-3,4-二羟基吡咯烷-2-基] -2-甲基-3-糠酸酯和酰胺容易从D-葡萄糖衍生而来，是选择性的竞争性抑制剂（K（i）>或= 3 microM）来自牛附睾和人胎盘的α-L-岩藻糖苷酶。
• Synthesis and Glycosidase Inhibitory Activities of 5-(1′,4′-Dideoxy-1′,4′-imino-D-erythrosyl)-2-methyl-3-furoic Acid (=5-[(3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-2-methylfuran-3-carboxylic Acid) Derivatives: New Leads as Selective -L-Fucosidase and -Galactosidase Inhibitors
  作者：Antonio J. Moreno-Vargas、Inmaculada Robina、Raynald Demange、Pierre Vogel

  DOI：10.1002/hlca.200390152

  日期：2003.6

  The García-González reaction of D-glucose and ethyl acetoacetate generated ethyl 5-[(1′S)-D-erythrosyl]-2-methyl-3-furoate (5), which was converted to ethyl 5-[(1′R)-1′,4′-dideoxy-1′,4′-imino-D-erythrosyl]-2-methyl-3-furoate (3c) and to ethyl 5-[(1′S)-1′,4′-dideoxy-1′,4′-imino-D-erythrosyl]-2-methyl-3-furoate (4c). Similar methods were developed to generate other carboxylic acid derivatives such as

  D-葡萄糖与乙酰乙酸乙酯的García-González反应生成5-[（1 'S）-D-赤藓糖基] -2-甲基-3-糠酸乙酯（5），然后将其转化为5-[（1' R）-1'，4'-二脱氧-1'，4'-亚氨基-D-赤藓基] -2-甲基-3-糠酸酯（3c）和乙基5-[（1 'S）-1'，4 ′-二脱氧-1′，4′-亚氨基-D-赤藓糖基] -2-甲基-3-糠酸酯（4c）。开发了类似的方法来生成其他羧酸衍生物，例如甲基（参见3e和4e），异丙基（参见3f）和丁酯（参见3g），S-苯基（参见3a）和S-乙基硫酯（请参见3m），N-苄基甲酰胺3b和4b，甘氨酸衍生的酰胺3h和N-苯基（请参见3i），N-异丙基（请参见3j和4j），N，N-二乙基-（请参见3k和4k）和N-乙基羧酰胺（参见3l）。所有新的5-（1'，4'-dideoxy-1'，4'-亚氨基-D-赤藓糖基）-3-糠酸（= 5-[（3 S，4
• Hetaryleneaminopolyols and Hetarylenecarbopeptoids:  a New Type of Glyco- and Peptidomimetics. Syntheses and Studies on Solution Conformation and Dynamics
  作者：Antonio J. Moreno-Vargas、Jesús Jiménez-Barbero、Inmaculada Robina

  DOI：10.1021/jo026631o

  日期：2003.5.1

  Ready access to a new class of oligomers has been demonstrated by the synthesis of hetarylene-aminopolyols and hetarylenecarbopeptoids using 3-hydroxymethyl-5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methylfuran and 5-(4-amino-4-deoxy-D-arabinotetritol-1-yl)-2-methyl-3-furoic acid as novel scaffolds. The conformational behavior of peptidomimetics 22, 23, 25, 26, and 36 have been analyzed by NMR spectroscopy and extensive molecular dynamics simulations. MD simulations using the GB/SA continuum solvent model for water and the MM3* force field provide a population distribution of conformers which satisfactorily agrees with the experimental NMR data for the torsional degrees of freedom of the molecule.
• Synthesis of [(2S,3S,4R)-3,4-Dihydroxypyrrolidin-2-yl]-5-methylfuran-4-carboxylic Acid Derivatives: New Leads as Selective β-Galactosidase Inhibitors
  作者：Antonio J. Moreno-Vargas、Raynald Demange、José Fuentes、Inmaculada Robina、Pierre Vogel

  DOI：10.1016/s0960-894x(02)00397-9

  日期：2002.9

  The preparation of [(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]furan derivatives in a stereoselective route starting from D-glucose and ethyl acetoacetate is presented. Ethyl ester (6), N,N-diethylamide (7) and N-isopropylamide (8) have been tested towards 25 glycosidases. Ester (6) is a selective inhibitor of beta-galactosidases. The new compounds represent a new type of imino-C-nucleoside analogues. (C) 2002 Published by Elsevier Science Ltd.