4α-benzyl-2-(3,4-O-isopropylidene-1,2,3,4-tetrahydroxybutyl)-6β-methoxy-3α-propylthio-1-aza-bicyclo<3.2.0>heptan-7-one

• 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: 4α-benzyl-2-(3,4-O-isopropylidene-1,2,3,4-tetrahydroxybutyl)-6β-methoxy-3α-propylthio-1-aza-bicyclo<3.2.0>heptan-7-one
• 英文别名: (2R,3S,4S,5R,6S)-4-benzyl-2-[(1R,2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-dihydroxyethyl]-6-methoxy-3-propylsulfanyl-1-azabicyclo[3.2.0]heptan-7-one
• 化学式: C₂₄H₃₅NO₆S
• 分子量: 465.611
• InChiKey: ANECNMSISKJFFZ-UESMIQOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4α-benzyl-2-(3,4-O-isopropylidene-1,2,3,4-tetrahydroxybutyl)-6β-methoxy-3α-propylthio-1-aza-bicyclo<3.2.0>heptan-7-one 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4α-benzyl-6β-methoxy-7-oxo-1-aza-bicyclo<3.2.0>hept-2-ene-2-carbaldehyde
  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：

  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 在 Bu₃NF 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以65%的产率得到4α-benzyl-2-(3,4-O-isopropylidene-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

文献信息

• Different approaches to the asymmetric synthesis of 1,3,6-trisubstituted and 1,2,3,6-tetrasubstituted carbapenems1 from D-glucosamine
  作者：Josefa Anaya、Derek H.R Barton、Stephane D Gero、Manuel Grande、JoséI.M Hernando、Nieves M Laso

  DOI：10.1016/0957-4166(95)00045-q

  日期：1995.2

  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.