[(2R,3R,4R,5R,6S)-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-6-phenylsulfanyl-4-prop-2-enoxyoxan-2-yl]methyl 4-(benzylamino)-4-oxobutanoate | 556039-04-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R,5R,6S)-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-6-phenylsulfanyl-4-prop-2-enoxyoxan-2-yl]methyl 4-(benzylamino)-4-oxobutanoate
• CAS: 556039-04-4
• 化学式: C₃₄H₃₉NO₈S
• 分子量: 621.752
• InChiKey: CJXBJVUEXHUEPD-MQEMTDQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R,6S)-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-6-phenylsulfanyl-4-prop-2-enoxyoxan-2-yl]methyl 4-(benzylamino)-4-oxobutanoate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.0h， 以65%的产率得到[(2R,3S,4R,5R,6S)-4,5-dihydroxy-3-[(4-methoxyphenyl)methoxy]-6-phenylsulfanyloxan-2-yl]methyl 4-(benzylamino)-4-oxobutanoate
  参考文献：
  名称：

  d‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase

  摘要：

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.

  DOI：

  10.1081/car-120019014
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 sodium 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 35.0h， 生成 [(2R,3R,4R,5R,6S)-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-6-phenylsulfanyl-4-prop-2-enoxyoxan-2-yl]methyl 4-(benzylamino)-4-oxobutanoate
  参考文献：
  名称：

  d‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase

  摘要：

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.

  DOI：

  10.1081/car-120019014

文献信息

• <scp>d</scp>‐Glucose as a Regioselectively Addressable Scaffold for Combinatorial Chemistry on Solid Phase
  作者：Francesco Peri、Francesco Nicotra、Colin P. Leslie、Fabrizio Micheli、Pierfausto Seneci、Carla Marchioro

  DOI：10.1081/car-120019014

  日期：2003.1.3

  D-Glucose derivatives bearing an anomeric thiophenyl group and orthogonally protections on secondary hydroxyl groups were linked to solid supports (PS/DV polymer, tentagel resin) through an ester bond on C-6. It was investigated the possibility to remove orthogonally protecting groups and functionalize selectively the free hydroxyls groups and the anomeric carbon of sugars in solid phase.