benzyl 2,3,4-tri-O-benzyl-7-deoxy-7-diazo-α-D-mannoheptopyran-6-ulose | 858352-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4-tri-O-benzyl-7-deoxy-7-diazo-α-D-mannoheptopyran-6-ulose
• 英文别名: 2-diazo-1-[(2S,3S,4S,5S,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxan-2-yl]ethanone
• CAS: 858352-15-5
• 化学式: C₃₅H₃₄N₂O₆
• 分子量: 578.665
• InChiKey: LMRFPIAGMJRUJU-VABIIVNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-7-deoxy-7-diazo-α-D-mannoheptopyran-6-ulose 、 磷酸二苄酯 在 sodium tetrahydroborate 作用下， 以 甲苯 、 乙醇 为溶剂， 反应 3.0h， 生成 benzyl 2,3,4-tri-O-benzyl-7-O-dibenzylphosphono-D-glycero-α-D-mannoheptopyranose 、 benzyl 2,3,4-tri-O-benzyl-7-O-dibenzylphosphono-L-glycero-α-D-mannoheptopyranose
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of ADP-d-glycero-β-d-manno-Heptose and a Mechanistic Study of ADP-l-glycero-d-manno-Heptose 6-Epimerase

  摘要：

  [GRAPHICS]A chemoenzymatic synthesis of ADP-D-glycero-beta-D-manno-heptose (ADP-D,D-Hep) is described in which D,D-Hep 7-phosphate is converted to ADP-D,D-Hep by two biosynthetic enzymes. This strategy allows access to the 6"-deuterated analogue, which upon incubation with the epimerase showed complete retention of the isotopic label at the 6"-position. This provides evidence for a direct oxidation mechanism in which the hydride initially transferred to the NADP(+) cofactor is subsequently returned to the same carbon in a nonstereospecific manner.

  DOI：

  10.1021/ol050774q
• 作为产物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 potassium dichromate 、 草酰氯 、 硫酸 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.25h， 生成 benzyl 2,3,4-tri-O-benzyl-7-deoxy-7-diazo-α-D-mannoheptopyran-6-ulose
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of ADP-d-glycero-β-d-manno-Heptose and a Mechanistic Study of ADP-l-glycero-d-manno-Heptose 6-Epimerase

  摘要：

  [GRAPHICS]A chemoenzymatic synthesis of ADP-D-glycero-beta-D-manno-heptose (ADP-D,D-Hep) is described in which D,D-Hep 7-phosphate is converted to ADP-D,D-Hep by two biosynthetic enzymes. This strategy allows access to the 6"-deuterated analogue, which upon incubation with the epimerase showed complete retention of the isotopic label at the 6"-position. This provides evidence for a direct oxidation mechanism in which the hydride initially transferred to the NADP(+) cofactor is subsequently returned to the same carbon in a nonstereospecific manner.

  DOI：

  10.1021/ol050774q