methyl (5S)-2,3-O-isopropylidene-5-C-(2-methylphenyl)-α-D-lyxofuranoside | 1385036-01-0

• 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: methyl (5S)-2,3-O-isopropylidene-5-C-(2-methylphenyl)-α-D-lyxofuranoside
• 英文别名: (S)-[(3aS,4S,6R,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-(2-methylphenyl)methanol
• CAS: 1385036-01-0
• 化学式: C₁₆H₂₂O₅
• 分子量: 294.348
• InChiKey: OCIHXRQMLJCDCJ-AICCOOGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基苯硼酸 、 1-O-methyl-2,3-O-isopropylidene-α-D-mannopentoaldo-1,4-furanose 在 diethylzinc 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以78%的产率得到methyl (5S)-2,3-O-isopropylidene-5-C-(2-methylphenyl)-α-D-lyxofuranoside
  参考文献：
  名称：

  Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes

  摘要：

  The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products.

  DOI：

  10.1021/ol301724x

文献信息

• Reaction of selected carbohydrate aldehydes with benzylmagnesium halides: benzyl versus <i>o</i>-tolyl rearrangement
  作者：Maroš Bella、Bohumil Steiner、Vratislav Langer、Miroslav Koóš

  DOI：10.3762/bjoc.10.202

  日期：——

  The Grignard reaction of 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside and benzylmagnesium chloride (or bromide) afforded a non-separable mixture of diastereomeric benzyl carbinols and diastereomeric o-tolyl carbinols. The latter resulted from an unexpected benzyl to o-tolyl rearrangement. The proportion of benzyl versus o-tolyl derivatives depended on the reaction conditions. Benzylmagnesium

  2,3-O-异亚丙基-α-D-lyxo-pentodialdo-1,4-呋喃糖苷和苄基氯化镁（或溴化物）的格氏反应提供了非对映异构苄基甲醇和非对映异构邻甲苯基甲醇的不可分离混合物。后者是由意外的苄基到邻甲苯基重排引起的。苄基与邻甲苯基衍生物的比例取决于反应条件。苄基氯化镁主要提供邻甲苯基甲醇，而使用苄基溴化镁优选仅在过量使用或在更高温度下使用时产生邻甲苯基甲醇。苄基和邻甲苯基衍生物的结构通过 NMR 光谱数据和 X 射线晶体学分析明确证实了它们的 5-酮类似物是通过氧化相应的非对映异构甲醇混合物获得的。
• Diastereoselective Addition of Arylzinc Reagents to Sugar Aldehydes
  作者：Ana D. Wouters、Diogo S. Lüdtke

  DOI：10.1021/ol301724x

  日期：2012.8.3

  The diastereoselective arylation of sugar-derived aldehydes is described. The arylating reagents are generated in situ by a boron-to-zinc exchange reaction of arylboronic acids with Et2Zn to generate arylethylzinc reagents. The exquisite reactivity of the arylzinc reagents allowed for an efficient and mild arylation, delivering the corresponding products in diastereolsomeric ratios of up to >20:1. The utility of the methodology is highlighted with an efficient formal synthesis of (+)-7-epl-goniofufurone, a member of the styryllactone family of natural products.