methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside | 540500-97-8

• 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-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-(1,3-dithian-2-ylmethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 540500-97-8
• 化学式: C₃₂H₃₈O₅S₂
• 分子量: 566.783
• InChiKey: YBXVLTYKHYIUSC-AIXQGADWSA-N

物化性质

• 沸点：
  675.3±55.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside 在 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 、 丁酮 为溶剂， 反应 1.58h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  ((2R,3R,4S,5S,6S)-3,4,5-三(苄氧基)-6-甲氧基四氢-2H-吡喃-2-基)甲醇 在 六甲基磷酰三胺 、 正丁基锂 、 2,6-二叔丁基-4-甲基吡啶 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297

文献信息

• A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives
  作者：Sébastien Vidal、Jean-Louis Montero、Alain Leydet、Alain Morère

  DOI：10.1080/10426500214297

  日期：2002.10

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.