(4S,5S,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(S)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane | 1417423-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5S,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(S)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane
• CAS: 1417423-83-6
• 化学式: C₃₀H₄₀O₆S₂
• 分子量: 560.776
• InChiKey: ZELSZSGKZULNBO-IRGGMKSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S,5S,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(S)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以99%的产率得到(2S)-2-[(4S,5S,6S)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]-2-phenylmethoxyacetaldehyde
  参考文献：
  名称：

  Stereodivergent Synthesis of d,d- and l,l-glycero-β-allo-Heptopyranoses on a Dioxanone Scaffold

  摘要：

  We report a stereodivergent synthesis of both enantiomers of glycero-allo-heptose from 2,2-dimethyl-1,3-dioxan-5-one, a readily available nonchiral scaffold, and from two different synthetic equivalents of glyoxal: dimethoxyacetaldehyde and 1,3-dithiane-2-carboxaldehyde. The short synthetic sequence involves first a proline-mediated, and then a lithium enolate mediated aldol reaction at the alpha-and alpha'-positions of the dioxanone ring, respectively, and demonstrates the complementary nature of organocatalysis and metal enolate based methods.

  DOI：

  10.1055/s-0032-1290461
• 作为产物：
  描述：

  (S)-4-((R)-1-(tert-butyldimethylsilyloxy)-2,2-dimethoxyethyl)-2,2-dimethyl-1,3-dioxan-5-one 在 sodium tetrahydroborate 、 正丁基锂 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 溶剂黄146 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 99.25h， 生成 (4S,5S,6S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[(S)-1,3-dithian-2-yl(phenylmethoxy)methyl]-2,2-dimethyl-5-phenylmethoxy-1,3-dioxane
  参考文献：
  名称：

  Stereodivergent Synthesis of d,d- and l,l-glycero-β-allo-Heptopyranoses on a Dioxanone Scaffold

  摘要：

  We report a stereodivergent synthesis of both enantiomers of glycero-allo-heptose from 2,2-dimethyl-1,3-dioxan-5-one, a readily available nonchiral scaffold, and from two different synthetic equivalents of glyoxal: dimethoxyacetaldehyde and 1,3-dithiane-2-carboxaldehyde. The short synthetic sequence involves first a proline-mediated, and then a lithium enolate mediated aldol reaction at the alpha-and alpha'-positions of the dioxanone ring, respectively, and demonstrates the complementary nature of organocatalysis and metal enolate based methods.

  DOI：

  10.1055/s-0032-1290461