6-deoxy-6-{(R)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfinyl}-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 1429934-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-deoxy-6-{(R)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfinyl}-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS: 1429934-54-2
• 化学式: C₂₂H₃₈O₆S
• 分子量: 430.606
• InChiKey: REBGCDBZYFOYOH-VXDAOUFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-{(R)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfinyl}-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 72.0h， 以99%的产率得到6-deoxy-6-{(R)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfinyl}-D-galactopyranose
  参考文献：
  名称：

  Synthesis and asymmetric oxidation of thioglycosides derived from neomenthanethiol and α-d-galactose

  摘要：

  6-Deoxy-6-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranose was synthesized in 94% yield from 1,2 : 3,4-di-O-isopropylidene-alpha-d-galactopyranose and neomenthanethiol, and its oxidation gave the corresponding diastereoisomeric sulfoxides in up to 84% yield and de values of up to 52%. The isopropylidene protective groups were removed from the sulfide and sulfoxides by treatment with trifluoroacetic acid in chloroform.

  DOI：

  10.1134/s1070428013030093
• 作为产物：
  描述：

  6-脱氧-6-碘-1,2:3,4-二-o-异亚丙基-α-d-半乳糖吡喃糖苷 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 、 四丁基碘化铵 、 caesium carbonate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 51.16h， 生成 6-deoxy-6-{(R)-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]sulfinyl}-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and asymmetric oxidation of thioglycosides derived from neomenthanethiol and α-d-galactose

  摘要：

  6-Deoxy-6-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-1,2:3,4-di-O-isopropylidene-alpha-d-galactopyranose was synthesized in 94% yield from 1,2 : 3,4-di-O-isopropylidene-alpha-d-galactopyranose and neomenthanethiol, and its oxidation gave the corresponding diastereoisomeric sulfoxides in up to 84% yield and de values of up to 52%. The isopropylidene protective groups were removed from the sulfide and sulfoxides by treatment with trifluoroacetic acid in chloroform.

  DOI：

  10.1134/s1070428013030093