benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside | 537036-60-5

• 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(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside
• 英文别名: (E)-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2S,3S,4S,5S,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxan-2-yl]prop-2-en-1-one
• CAS: 537036-60-5
• 化学式: C₄₆H₅₂O₁₀
• 分子量: 764.913
• InChiKey: QMUXUYHSJKVQKH-LBXBOFDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside 在 zinc(II) tetrahydroborate 、 臭氧 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside
  参考文献：
  名称：

  Convenient approach to higher carbon sugars. First synthesis of the free C12-sugar: d-erythro-l-manno-d-manno-dodecose

  摘要：

  The model synthesis of a C12-aldose was initiated from the easily available dimethyl(benzyl 2,3,4-tri-O-benzyl-alpha-D-manno-heptopyranos-6-ulos-7-yl)phosphonate and 2,3:4,5-di-O-isopropylidene-D-arabinose. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00484-6
• 作为产物：
  描述：

  dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate 、 2,3-二氟-6-硝基苯胺 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到benzyl 2,3,4-tri-O-benzyl-7(E)-dideoxy-7(E)-eno-9,10:11,12-di-O-isopropylidene-6-oxo-D-arabino-α-D-manno-dodeca-1,5-pyranoside
  参考文献：
  名称：

  Convenient approach to higher carbon sugars. First synthesis of the free C12-sugar: d-erythro-l-manno-d-manno-dodecose

  摘要：

  The model synthesis of a C12-aldose was initiated from the easily available dimethyl(benzyl 2,3,4-tri-O-benzyl-alpha-D-manno-heptopyranos-6-ulos-7-yl)phosphonate and 2,3:4,5-di-O-isopropylidene-D-arabinose. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(02)00484-6

文献信息

• Convenient approach to higher carbon sugars. First synthesis of the free C12-sugar: d-erythro-l-manno-d-manno-dodecose
  作者：Sławomir Jarosz、Stanisław Skóra、Izabela Kościołowska

  DOI：10.1016/s0008-6215(02)00484-6

  日期：2003.2

  The model synthesis of a C12-aldose was initiated from the easily available dimethyl(benzyl 2,3,4-tri-O-benzyl-alpha-D-manno-heptopyranos-6-ulos-7-yl)phosphonate and 2,3:4,5-di-O-isopropylidene-D-arabinose. (C) 2003 Published by Elsevier Science Ltd.