1,4-anhydro-3-O-benzyl-2-deoxy-5-O-methoxymethyl-D-erythro-pent-1-enitol | 112289-61-9

• 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: 1,4-anhydro-3-O-benzyl-2-deoxy-5-O-methoxymethyl-D-erythro-pent-1-enitol
• 英文别名: (2R,3S)-2-(methoxymethoxymethyl)-3-phenylmethoxy-2,3-dihydrofuran
• CAS: 112289-61-9
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: DRIOPXULUFGAPB-UONOGXRCSA-N

物化性质

• 沸点：
  341.9±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-3-O-benzyl-2-deoxy-5-O-methoxymethyl-D-erythro-pent-1-enitol 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 1-O-acetyl-2-deoxy-2-fluoro-5-O-methoxymethyl-β-D-arabinofuranose
  参考文献：
  名称：

  次氯酸乙酰基与吡喃和呋喃糖的反应

  摘要：

  摘要乙酰基次萤石向戊基吡喃糖衍生的糖基的区域特异性顺式加成反应导致立体异构体的混合物。呋喃类糖发生立体特异性反应，加成方向受C-3取代基的性质支配。苄氧基从双键相对较少受阻的相反面引起侵蚀，而羟基则从同一侧诱导加成。从这些反应中，β-d-阿拉伯糖-，α-d-核糖-，β-d-lyxo-和α-d-木糖吡喃糖以及β-d-甘露糖的2-脱氧-2-氟衍生物。获得了α，d-葡萄糖，α-d-核糖和β-d-阿拉伯呋喃糖，并给出了它们的1 H-，13 C-和19 Fn.mr数据。

  DOI：

  10.1016/0008-6215(87)80196-9
• 作为产物：
  描述：

  2,3-O-(1-methylethylidene)-5-O-methoxymethyl-β-D-ribofuranosyl chloride 生成 1,4-anhydro-3-O-benzyl-2-deoxy-5-O-methoxymethyl-D-erythro-pent-1-enitol
  参考文献：
  名称：

  FURSTNER, ALOIS;WEIDMANN, HANS, J. CARBOHYDR. CHEM., 7,(1988) N, C. 773-783

  摘要：

  DOI：

文献信息

• Arylbis(arylthio)sulfonium salts as reagents for the synthesis of 2-deoxy-.beta.-glycosides
  作者：Gurmit Grewal、Neelu Kaila、Richard W. Franck

  DOI：10.1021/jo00033a033

  日期：1992.3

  The title sulfonium salts undergo electrophilic addition to glycals in the presence of alcohols to form principally beta-glycosides. A substituent effect study has shown that the reagent with a p-tolylthio group is the most face-selective. By variation of the alcohol nucleophile, it has been shown that face selectivity is also dependent on the structure of the nucleophile. One instance of double diastereodifferentiation was uncovered when the racemic alcohol 23.5 was used in a reaction with tribenzyl glucal 22.1. The effect of glycal substitution on the face selectivity has led to the postulation of a heretofore unrecognized and still unexplained stereoelectronic effect.
• Polarized-.pi. frontier molecular orbital (PPFMO) and experimental studies of facial selectivity in electrophilic attacks on substituted alkenes
  作者：Richard W. Franck、Neelu Kaila、Michael Blumenstein、Aloma Geer、Xiao Ling Huang、J. J. Dannenberg

  DOI：10.1021/jo00072a012

  日期：1993.9

  Polarized pi-frontier orbital theory (PPFMO) is applied to the protonation and sulfenylation of several dihydrofurans and dihydropyrans of importance in sugar chemistry. The PPFMO method correctly predicts the observed selectivities for all experimentally observed cases, two of which are reported here for the first time.