5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose | 137585-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose
• 英文别名: 1,2-O-isopropylidene-5-phenylmethyl-5-deoxy-α-D-xylofuranose；(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-phenylethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 137585-73-0
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: LGVDAYBLXLSJJQ-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 草酰氯 、 硫酸 、 二(3-甲基丁烷-2-基)硼烷 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 50.0h， 生成 ethyl (4S,5S)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2Z)-heptenoate
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-phenylethyl)-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以99%的产率得到5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n

文献信息

• 5-Deoxy-5-alkyl-1,2-O-isopropylidene-α-D-xylofuranoses as chiral auxiliaries in asymmetric 1,4-addition reaction
  作者：Yung-Son Hon、Fen-Ling Chen、Yih-Pyng Huang、Ta-Jung Lu

  DOI：10.1016/s0957-4166(00)82200-4

  日期：1991.1

  Two deoxy-sugar based chiral auxiliaries (2 and 5) have been prepared. Their alpha,beta-unsaturated esters were treated with different cuprate reagents to give the 1,4-addition adducts in good chemical yield and good diastereoselectivity.
• Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol
  作者：Ravi P. Singh、Vinod K. Singh

  DOI：10.1021/jo049858n

  日期：2004.5.1

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.