1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol | 275812-90-3

• 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: 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol
• 英文别名: N-[(1R)-1-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylethyl]-4-methylbenzenesulfonamide
• CAS: 275812-90-3
• 化学式: C₂₅H₃₃NO₆S
• 分子量: 475.606
• InChiKey: YDXPUKYYTAINCD-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  91.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol 在 Dowex 50X₈-200 作用下， 以 甲醇 为溶剂， 以82%的产率得到N-{(R)-1-[(4R,5R)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues

  摘要：

  1-Amino-1-deoxy-D-glucitol was converted into the selectively protected title compound 4, an N-tosyl-activated aziridine that readily underwent ring opening with various nucleophiles. Further deprotection of the 5,6-diol moiety followed by ring closure under Mitsunobu conditions afforded the corresponding 6-substituted analogues of 1-deoxymannojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00130-1
• 作为产物：
  描述：

  1-deoxy-3,4:5,6-di-O-isopropylidene-2-O-methanesulfonyl-1-(N-p-toluenesulfonyl)amino-D-glucitol 在 碘 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-C-phenyl-2-(N-p-toluenesulfonyl)amino-D-mannitol
  参考文献：
  名称：

  使用衍生自1-氨基-1-脱氧葡萄糖醇的N-甲苯磺酰基和N-壬烷基活化的氮丙啶合成1- deoxymannojirimycin类似物

  摘要：

  将3，4； 5，6-二异亚丙基保护的1-氨基-1-脱氧-d-葡萄糖醇转化为N-甲苯磺酰基和N- nosyl活化的氮丙啶中间体，它们通过与各种亲核试剂反应而开环。使用两种不同的活化6-OH的方法，将末端缩醛基团选择性水解得到的5,6-二醇进行（2-N→6-OH）环化。N-烷基和3，4-缩醛基团的最终脱保护顺利进行，得到1-脱氧甘露糖霉素的6-取代类似物。

  DOI：

  10.1016/s0040-4020(01)00650-0

文献信息

• Synthesis of 1-deoxymannojirimycin analogues using N -tosyl and N -nosyl activated aziridines derived from 1-amino-1-deoxyglucitol
  作者：Hua Mao、Gert J. Joly、Koen Peeters、Georges J. Hoornaert、Frans Compernolle

  DOI：10.1016/s0040-4020(01)00650-0

  日期：2001.8

  aziridine intermediates, which underwent ring opening by reaction with various nucleophiles. The 5,6-diols resulting from selective hydrolysis of the terminal acetal group were subjected to (2-N→6-OH) cyclisation using two different methods for activation of 6-OH. Final deprotection of the N-nosyl and 3,4-acetal group proceeded smoothly to afford 6-substituted analogues of 1-deoxymannojirimycin.

  将3，4； 5，6-二异亚丙基保护的1-氨基-1-脱氧-d-葡萄糖醇转化为N-甲苯磺酰基和N- nosyl活化的氮丙啶中间体，它们通过与各种亲核试剂反应而开环。使用两种不同的活化6-OH的方法，将末端缩醛基团选择性水解得到的5,6-二醇进行（2-N→6-OH）环化。N-烷基和3，4-缩醛基团的最终脱保护顺利进行，得到1-脱氧甘露糖霉素的6-取代类似物。
• Use of the N-tosyl-activated aziridine 1,2-dideoxy-1,2-iminomannitol as a synthon for 1-deoxymannojirimycin analogues
  作者：Gert J Joly、Koen Peeters、Hua Mao、Thierry Brossette、Georges J Hoornaert、Frans Compernolle

  DOI：10.1016/s0040-4039(00)00130-1

  日期：2000.3

  1-Amino-1-deoxy-D-glucitol was converted into the selectively protected title compound 4, an N-tosyl-activated aziridine that readily underwent ring opening with various nucleophiles. Further deprotection of the 5,6-diol moiety followed by ring closure under Mitsunobu conditions afforded the corresponding 6-substituted analogues of 1-deoxymannojirimycin. (C) 2000 Elsevier Science Ltd. All rights reserved.