1,2-O-Isopropyliden-6-O-methyl-5-desoxy-α-D-xylohexofuran-5-enose | 94844-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-Isopropyliden-6-O-methyl-5-desoxy-α-D-xylohexofuran-5-enose
• CAS: 94844-71-0
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: LLAYDJROWYDXLG-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2-O-Isopropyliden-6-O-methyl-5-desoxy-α-D-xylohexofuran-5-enose 在 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 2-碘苯甲酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 1,2-O-Isopropyliden-6-O-methyl-5-desoxy-α-D-xylohexofuran-5-enose
  参考文献：
  名称：

  General Homologation Strategy for Synthesis of l-glycero- and d-glycero-Heptopyranoses

  摘要：

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

  DOI：

  10.1021/acs.orglett.5b02620

文献信息

• General Homologation Strategy for Synthesis of <scp>l</scp>-<i>glycero</i>- and <scp>d</scp>-<i>glycero</i>-Heptopyranoses
  作者：Shaheen K. Mulani、Kuang-Chun Cheng、Kwok-Kong T. Mong

  DOI：10.1021/acs.orglett.5b02620

  日期：2015.11.20

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.