2,3,4,6-tetra-O-benzyloxycarbonyl-α-D-mannopyranosyl bromide | 914912-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyloxycarbonyl-α-D-mannopyranosyl bromide
• 英文别名: benzyl [(2R,3S,4S,5R,6R)-2-bromo-3,5-bis(phenylmethoxycarbonyloxy)-6-(phenylmethoxycarbonyloxymethyl)oxan-4-yl] carbonate
• CAS: 914912-54-2
• 化学式: C₃₈H₃₅BrO₁₃
• 分子量: 779.592
• InChiKey: IXCLDYBQVRTCGC-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyloxycarbonyl-α-D-mannopyranosyl bromide 、 methyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside 在 2,3,5-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到methyl 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Influence of the Benzyloxycarbonyl Protective Group on Glycosylation with Mannopyranosyl Donors

  摘要：

  The perbenzyloxycarbonylation of D-mannose, D-glucose, and D-galactose was achieved in high yield. In the mannose series, the selective removal of the anomeric benzyloxycarbonyl group followed by the activation of the anomeric position furnished, depending on the activation conditions, either a bromo glycosyl donor or a trichloroacetimidate donor. The trichloroacetimidate donor, protected by benzyloxycarbonyl groups, was used successfully for the synthesis of a disaccharide.[GRAPHICS]

  DOI：

  10.1080/07328300600859759
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyloxycarbonyl-D-mannopyranose 在 bismuth(III) chloride 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到2,3,4,6-tetra-O-benzyloxycarbonyl-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Influence of the Benzyloxycarbonyl Protective Group on Glycosylation with Mannopyranosyl Donors

  摘要：

  The perbenzyloxycarbonylation of D-mannose, D-glucose, and D-galactose was achieved in high yield. In the mannose series, the selective removal of the anomeric benzyloxycarbonyl group followed by the activation of the anomeric position furnished, depending on the activation conditions, either a bromo glycosyl donor or a trichloroacetimidate donor. The trichloroacetimidate donor, protected by benzyloxycarbonyl groups, was used successfully for the synthesis of a disaccharide.[GRAPHICS]

  DOI：

  10.1080/07328300600859759

文献信息

• Influence of the Benzyloxycarbonyl Protective Group on Glycosylation with Mannopyranosyl Donors
  作者：Alain Morère、Fouzi Mouffouk、Simon Leiris、Alain Leydet、Jean‐Louis Montero

  DOI：10.1080/07328300600859759

  日期：2006.8

  The perbenzyloxycarbonylation of D-mannose, D-glucose, and D-galactose was achieved in high yield. In the mannose series, the selective removal of the anomeric benzyloxycarbonyl group followed by the activation of the anomeric position furnished, depending on the activation conditions, either a bromo glycosyl donor or a trichloroacetimidate donor. The trichloroacetimidate donor, protected by benzyloxycarbonyl groups, was used successfully for the synthesis of a disaccharide.[GRAPHICS]