2-pentyl-(2-deoxy-5,6-O-isopropylidene-α-D-glucofurano)[2,1-d]2-oxazoline | 261729-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-pentyl-(2-deoxy-5,6-O-isopropylidene-α-D-glucofurano)[2,1-d]2-oxazoline
• 英文别名: (3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-pentyl-3a,5,6,6a-tetrahydrofuro[3,2-d][1,3]oxazol-6-ol
• CAS: 261729-08-2
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: LVWUEFVKAFXBGV-FZGMBXNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-pentyl-(2-deoxy-5,6-O-isopropylidene-α-D-glucofurano)[2,1-d]2-oxazoline 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以82%的产率得到2-deoxy-2-hexanoylamino-5,6-O-isopropylidene-D-glucofuranose
  参考文献：
  名称：

  Synthesis of 2-acylamino-2-deoxy-d-glucofuranoses and their transformation into hex-2-enofuranoses

  摘要：

  The preparation of 2-deoxy-2-hexanamido (octanamido, decanamido, dodecanamido)-5,6-isopropylidene-D-glucofuranoses (9-12) from the corresponding O-unprotected 2-acylamino-2-deoxy-D-glucopyranoses through the bicyclic glucofurano[2,1-d]oxazolines is reported. Compounds 9-12 are transformed into 2-acylamino-2-deoxy-2-enofuranoses by treatment with Amberlite IRA-400 (OH-) resin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00225-6
• 作为产物：
  描述：

  丙酮 、 N-hexanoyl glucosamine 在 三氯化铁 作用下， 反应 0.33h， 以55%的产率得到2-pentyl-(2-deoxy-5,6-O-isopropylidene-α-D-glucofurano)[2,1-d]2-oxazoline
  参考文献：
  名称：

  Synthesis of 2-acylamino-2-deoxy-d-glucofuranoses and their transformation into hex-2-enofuranoses

  摘要：

  The preparation of 2-deoxy-2-hexanamido (octanamido, decanamido, dodecanamido)-5,6-isopropylidene-D-glucofuranoses (9-12) from the corresponding O-unprotected 2-acylamino-2-deoxy-D-glucopyranoses through the bicyclic glucofurano[2,1-d]oxazolines is reported. Compounds 9-12 are transformed into 2-acylamino-2-deoxy-2-enofuranoses by treatment with Amberlite IRA-400 (OH-) resin. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00225-6

文献信息

• Synthesis of 2-acylamino-2-deoxy-d-glucofuranoses and their transformation into hex-2-enofuranoses
  作者：José G Fernández-Bolaños、Vı́ctor Ulgar、Inmaculada Robina、José Fuentes

  DOI：10.1016/s0008-6215(99)00225-6

  日期：1999.12

  The preparation of 2-deoxy-2-hexanamido (octanamido, decanamido, dodecanamido)-5,6-isopropylidene-D-glucofuranoses (9-12) from the corresponding O-unprotected 2-acylamino-2-deoxy-D-glucopyranoses through the bicyclic glucofurano[2,1-d]oxazolines is reported. Compounds 9-12 are transformed into 2-acylamino-2-deoxy-2-enofuranoses by treatment with Amberlite IRA-400 (OH-) resin. (C) 1999 Elsevier Science Ltd. All rights reserved.