(R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[3-(hydroxymethyl)-5,6-dihydro-1,4-dithiin-2-yl]methyl acetate | 1219030-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[3-(hydroxymethyl)-5,6-dihydro-1,4-dithiin-2-yl]methyl acetate
• 英文别名: [(R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-[6-(hydroxymethyl)-2,3-dihydro-1,4-dithiin-5-yl]methyl] acetate
• CAS: 1219030-97-3
• 化学式: C₁₃H₂₀O₅S₂
• 分子量: 320.431
• InChiKey: OGMFPASJNFDJBR-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[3-(hydroxymethyl)-5,6-dihydro-1,4-dithiin-2-yl]methyl acetate 在 吡啶 、 pyridinium chlorochromate 作用下， 反应 8.0h， 以89%的产率得到(R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(3-formyl-5,6-dihydro-1,4-dithiin-2-yl)methyl acetate
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k
• 作为产物：
  描述：

  (R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(3-[(4-methoxybenzyl)oxy]methyl-5,6-dihydro-1,4-dithiin-2-yl)methyl acetate 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到(R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[3-(hydroxymethyl)-5,6-dihydro-1,4-dithiin-2-yl]methyl acetate
  参考文献：
  名称：

  Highly Stereoselective de Novo Synthesis of l-Hexoses

  摘要：

  An efficient and general de novo synthetic route to enantiomerically pure L-hexoses has been accomplished starting from the heterocyclic homologating agent 5,6-dihydro-1,4-dithiin-2-yl[(4-methoxybentyl)oxy]methane and methyl alpha,beta-isopropylidene-L-glycerate. The sugar scaffold was constructed by an acid-catalyzed domino reaction, which enabled selective preparation of either methyl 2,3-dideoxy-alpha-L-threohex-2-enopyranosides or 1,6-anhydro-2,3-dideoxy-beta-L-threo-hex-2-enopyranose as key intermediates. The subsequent double bond functionalization by syn or anti dihydroxylation reactions allowed introduction of the remaining stereogenic centers, leading to desired orthogonally protected L-hexopyranosides with a high degree of diastereoselectivity and with very good overall yields. These and previous results (based on the use of the corresponding L-erythro epimers) contribute to make our approach general and place it among the few methods able to synthesize the whole series of the rare L-hexoses.

  DOI：

  10.1021/jo100077k