(2'S)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose | 139973-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[[(2S)-oxiran-2-yl]methoxy]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 139973-62-9
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: UJYWGCVKPNGAIK-JSAZDUPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'S)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (2'S)-1,2-O-isopropylidene-3-O-[3'-{1-(2-pyridyl)piperazin-4-yl}-2'-hydroxy-propan-1'-yl]-α-D-glucofuranose
  参考文献：
  名称：

  Syntheses and immunomodulatory activity of 3-O-[2′-hydroxy-3′-N,N-disubstituted aminopropan-1′-yl]-α-d-glucofuranoses

  摘要：

  A number of 3-O-[2 ' -hydroxy-3 ' -N,N-aminopropan-l ' -yl]-alpha -D-glucofuranoses were synthesised by regioselective oxirane ring opening in compound 2 with different secondary amines followed by selective deacetalisation. All the compounds were tested for their immunomodulatory potential in vitro; seven of them expressed significant immunostimulant activity. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01234-x
• 作为产物：
  描述：

  右旋环氧氯丙烷 、 双丙酮葡萄糖 在 sodium hydroxide 、 四丁基溴化铵 作用下， 反应 12.5h， 以60%的产率得到(2'S)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose
  参考文献：
  名称：

  Syntheses and immunomodulatory activity of 3-O-[2′-hydroxy-3′-N,N-disubstituted aminopropan-1′-yl]-α-d-glucofuranoses

  摘要：

  A number of 3-O-[2 ' -hydroxy-3 ' -N,N-aminopropan-l ' -yl]-alpha -D-glucofuranoses were synthesised by regioselective oxirane ring opening in compound 2 with different secondary amines followed by selective deacetalisation. All the compounds were tested for their immunomodulatory potential in vitro; seven of them expressed significant immunostimulant activity. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01234-x

文献信息

• Khan; Tripathi; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 405 - 408
  作者：Khan、Tripathi、Bhaduri

  DOI：——

  日期：——
• Syntheses and immunomodulatory activity of 3-O-[2′-hydroxy-3′-N,N-disubstituted aminopropan-1′-yl]-α-d-glucofuranoses
  作者：Abdul Rehman Khan、Rama Pati Tripathi、Amiya Prasad Bhaduri、Ragini Sahai、Anju Puri、Lalit Mohan Tripathi、Vishwa Mohan Lal Srivastava

  DOI：10.1016/s0223-5234(01)01234-x

  日期：2001.5

  A number of 3-O-[2 ' -hydroxy-3 ' -N,N-aminopropan-l ' -yl]-alpha -D-glucofuranoses were synthesised by regioselective oxirane ring opening in compound 2 with different secondary amines followed by selective deacetalisation. All the compounds were tested for their immunomodulatory potential in vitro; seven of them expressed significant immunostimulant activity. (C) 2001 Editions scientifiques et medicales Elsevier SAS.