methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose | 1049006-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose
• 英文别名: (E,4S,5R,6R)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2S,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-4,5,6-tris(phenylmethoxy)hex-2-en-1-one
• CAS: 1049006-95-2
• 化学式: C₅₉H₆₄O₁₁
• 分子量: 949.151
• InChiKey: OZUPAAJQHFEKPS-KKKBVCPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  70
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose 在 zinc(II) tetrahydroborate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以47.6%的产率得到(E,1R,4S,5R,6R)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(2R,3S,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]-4,5,6-tris(phenylmethoxy)hex-2-en-1-ol
  参考文献：
  名称：

  Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols

  摘要：

  Coupling of a sugar phosphonate with a sugar aldehyde afforded a C-13-higher sugar enone. Reduction of the carbonyl function provided both stereoisomeric allylic alcohols. Inversion of the configuration at the carbinol centre in these derivatives did not yield the expected S(N)2 product, but proceeded with rearrangement to the tetrahydrofuran derivative. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.05.010
• 作为产物：
  描述：

  (2R,3S,4R)-2,3,4-tris(benzyloxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)butanal 、 dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以84%的产率得到methyl 2,3,4,9,10,11-hexa-O-benzyl-7,8-dideoxy-7,8-didehydro-12,13-O-isopropylidene-α-D-gluco-D-gluco-tridec-7(E)-eno-1,5-pyranosid-6-ulose
  参考文献：
  名称：

  Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols

  摘要：

  Coupling of a sugar phosphonate with a sugar aldehyde afforded a C-13-higher sugar enone. Reduction of the carbonyl function provided both stereoisomeric allylic alcohols. Inversion of the configuration at the carbinol centre in these derivatives did not yield the expected S(N)2 product, but proceeded with rearrangement to the tetrahydrofuran derivative. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2008.05.010

文献信息

• Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols
  作者：Slawomir Jarosz、Agnieszka Gajewska、Roman Luboradzki

  DOI：10.1016/j.tetasy.2008.05.010

  日期：2008.6

  Coupling of a sugar phosphonate with a sugar aldehyde afforded a C-13-higher sugar enone. Reduction of the carbonyl function provided both stereoisomeric allylic alcohols. Inversion of the configuration at the carbinol centre in these derivatives did not yield the expected S(N)2 product, but proceeded with rearrangement to the tetrahydrofuran derivative. (C) 2008 Published by Elsevier Ltd.