1-<1-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-trihydroxybutyl)-1-<1,3>dithian-2-yl-1,1-dihydroxy-methyl>-3β-methoxy-4β-styryl-azetidin-2-one | 162584-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-<1-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-trihydroxybutyl)-1-<1,3>dithian-2-yl-1,1-dihydroxy-methyl>-3β-methoxy-4β-styryl-azetidin-2-one
• 英文别名: (3S,4R)-1-[(1R,2R,3R)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(1,3-dithian-2-yl)-2,3-bis(triethylsilyloxy)propyl]-3-methoxy-4-[(E)-2-phenylethenyl]azetidin-2-one
• CAS: 162584-36-3
• 化学式: C₃₆H₆₁NO₆S₂Si₂
• 分子量: 724.186
• InChiKey: MIUMGIPZIGQNNN-SGWQEOOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.42
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-<1-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-trihydroxybutyl)-1-<1,3>dithian-2-yl-1,1-dihydroxy-methyl>-3β-methoxy-4β-styryl-azetidin-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以70%的产率得到4α-benzyl-2-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-tetrahydroxybutyl)-6β-methoxy-3α-propylthio-1-aza-bicyclo<3.2.0>heptan-7-one
  参考文献：
  名称：

  Different approaches to the asymmetric synthesis of 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems1 from D-glucosamine

  摘要：

  Different stereocontrolled syntheses of optically active 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems(1) are reported. D-glucosamine, as chiral auxiliary, trans-cinnamaldehyde and methoxyacetyl chloride were used as starting materials in the Staudinger ketene-imine monobactam formation. Radical cyclization and oxidation reactions led to the desired carbapenems.

  DOI：

  10.1016/0957-4166(95)00045-q
• 作为产物：
  描述：

  甲氧基乙酰氯 、 [(1R,2R,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-[1,3]dithian-2-yl-2,3-bis-triethylsilanyloxy-propyl]-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine 在 TEA 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 1-<1-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-trihydroxybutyl)-1-<1,3>dithian-2-yl-1,1-dihydroxy-methyl>-3β-methoxy-4β-styryl-azetidin-2-one 、 1-<1-(3,4-O-isopropylidene-1,2-di-O-triethylsilyl-1,2,3,4-tetroxydroxybutyl)-1-<1,3>dithian-2-yl-1,1-dihydroxymethyl>-3α-methoxy-4α-styryl-azetidin-2-one
  参考文献：
  名称：

  Different approaches to the asymmetric synthesis of 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems1 from D-glucosamine

  摘要：

  Different stereocontrolled syntheses of optically active 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems(1) are reported. D-glucosamine, as chiral auxiliary, trans-cinnamaldehyde and methoxyacetyl chloride were used as starting materials in the Staudinger ketene-imine monobactam formation. Radical cyclization and oxidation reactions led to the desired carbapenems.

  DOI：

  10.1016/0957-4166(95)00045-q