2-naphthyl 3,4-O-isopropylidene-β-D-xylopyranoside | 1632131-36-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-naphthyl 3,4-O-isopropylidene-β-D-xylopyranoside
• 英文别名: (3aR,6S,7R,7aR)-2,2-dimethyl-6-naphthalen-2-yloxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 1632131-36-2
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: ZSPMZHZVZKDJMB-NCOADZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-naphthyl 3,4-O-isopropylidene-β-D-xylopyranoside 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 (3aR,6S,7aS)-2,2-dimethyl-6-(naphthalen-2-yloxy)dihydro-4H-[1,3]dioxolo[4,5-c]pyran-7(6H)-one
  参考文献：
  名称：

  Release of Ring Strain as Driving Force for Inversion of Stereochemistry – Application to the Synthesis of Ribopyranosides from Xylopyranosides

  摘要：

  By using a Swern oxidation-epimerization-reduction sequence it is possible to selectively epimerize any position in isopropylidene-protected xylopyranosides, thus forming arabinosides, ribosides, and lyxosides. The driving force for epimerization of position 3 (xylo to ribo) is the release of ring strain by going from a 1,2-trans-acetal to a 1,2-cis-acetal.

  DOI：

  10.1055/s-0033-1341203
• 作为产物：
  描述：

  2-甲氧基丙烯 、 naphth-2-yl β-D-xylopyranoside 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-naphthyl 2,3-O-isopropylidene-β-D-xylopyranoside 、 2-naphthyl 3,4-O-isopropylidene-β-D-xylopyranoside
  参考文献：
  名称：

  Release of Ring Strain as Driving Force for Inversion of Stereochemistry – Application to the Synthesis of Ribopyranosides from Xylopyranosides

  摘要：

  By using a Swern oxidation-epimerization-reduction sequence it is possible to selectively epimerize any position in isopropylidene-protected xylopyranosides, thus forming arabinosides, ribosides, and lyxosides. The driving force for epimerization of position 3 (xylo to ribo) is the release of ring strain by going from a 1,2-trans-acetal to a 1,2-cis-acetal.

  DOI：

  10.1055/s-0033-1341203

文献信息

• Release of Ring Strain as Driving Force for Inversion of Stereochemistry – Application to the Synthesis of Ribopyranosides from Xylopyranosides
  作者：Ulf Ellervik、Sophie Manner

  DOI：10.1055/s-0033-1341203

  日期：——

  By using a Swern oxidation-epimerization-reduction sequence it is possible to selectively epimerize any position in isopropylidene-protected xylopyranosides, thus forming arabinosides, ribosides, and lyxosides. The driving force for epimerization of position 3 (xylo to ribo) is the release of ring strain by going from a 1,2-trans-acetal to a 1,2-cis-acetal.