5-O-benzhydryl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol | 1202748-20-6

• 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: 5-O-benzhydryl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol
• 英文别名: [(4S,5S)-5-[(1R)-2-benzhydryloxy-1-methylsulfonyloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate
• CAS: 1202748-20-6
• 化学式: C₂₃H₃₀O₉S₂
• 分子量: 514.618
• InChiKey: GBPJHQSKEKOKDL-VWPQPMDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-O-benzhydryl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol 、 苄胺 反应 18.0h， 以86%的产率得到5-O-benzhydryl-N-benzyl-2,3-O-isopropylidene-1,4-dideoxy-1,4-imino-L-lyxitol
  参考文献：
  名称：

  Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

  摘要：

  Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-L-lyxitol (LIL). DIL showed potent [K-i = 0.13 mu M]-and LIL showed weak [K-i = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K-i = 64 mu M] and N-benzyl-LIL [K-i = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.004
• 作为产物：
  描述：

  5-O-benzhydryl-2,3-O-isopropylidene-D-ribitol 、 甲基磺酰氯 在 吡啶 作用下， 反应 2.5h， 以93%的产率得到5-O-benzhydryl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-D-ribitol
  参考文献：
  名称：

  Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

  摘要：

  Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-L-lyxitol (LIL). DIL showed potent [K-i = 0.13 mu M]-and LIL showed weak [K-i = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K-i = 64 mu M] and N-benzyl-LIL [K-i = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.004