2,5-anhydro-1-[(diethoxyphosphoryl)amino]-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate | 276682-96-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 2,5-anhydro-1-[(diethoxyphosphoryl)amino]-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate
• 英文别名: S-[(2R,3R)-2-[(diethoxyphosphorylamino)methyl]oxolan-3-yl] ethanethioate
• CAS: 276682-96-3
• 化学式: C₁₁H₂₂NO₅PS
• 分子量: 311.339
• InChiKey: QIJGIRBUAUBKLW-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-1-[(diethoxyphosphoryl)amino]-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate 在 盐酸 作用下， 以 甲苯 为溶剂， 以14 g的产率得到2,5-anhydro-1-amino-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate hydrochloride
  参考文献：
  名称：

  Suppression of Ethyl Migration in the Synthesis of 2,5-Anhydro-1-Amino-1,4-Dideoxy-3-Thio-D-Threo-Pentitol Hydrochloride, A Key Intermediate for Oral the 1β-Methylcarbapenems

  摘要：

  A reproducible synthesis of 2,5-anhydro-1-amino-1,4-dideoxy-3-thio-D-threo-pentitol hydrochloride (2b) via the Staudinger reaction with triethyl phosphite was developed. An unexpected ethyl migration from an oxygen to the nitrogen of iminophosphorane 7 was observed.

  DOI：

  10.1080/00397910008087144
• 作为产物：
  描述：

  2,5-anhydro-1-azido-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate 、 亚磷酸三乙酯 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以100%的产率得到2,5-anhydro-1-[(diethoxyphosphoryl)amino]-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate
  参考文献：
  名称：

  Suppression of Ethyl Migration in the Synthesis of 2,5-Anhydro-1-Amino-1,4-Dideoxy-3-Thio-D-Threo-Pentitol Hydrochloride, A Key Intermediate for Oral the 1β-Methylcarbapenems

  摘要：

  A reproducible synthesis of 2,5-anhydro-1-amino-1,4-dideoxy-3-thio-D-threo-pentitol hydrochloride (2b) via the Staudinger reaction with triethyl phosphite was developed. An unexpected ethyl migration from an oxygen to the nitrogen of iminophosphorane 7 was observed.

  DOI：

  10.1080/00397910008087144

文献信息

• Suppression of Ethyl Migration in the Synthesis of 2,5-Anhydro-1-Amino-1,4-Dideoxy-3-Thio-D-Threo-Pentitol Hydrochloride, A Key Intermediate for Oral the 1β-Methylcarbapenems
  作者：Panayota Bitha、Timothy W. Strohmeyer、Zhong Li、Yang-I Lin

  DOI：10.1080/00397910008087144

  日期：2000.4

  A reproducible synthesis of 2,5-anhydro-1-amino-1,4-dideoxy-3-thio-D-threo-pentitol hydrochloride (2b) via the Staudinger reaction with triethyl phosphite was developed. An unexpected ethyl migration from an oxygen to the nitrogen of iminophosphorane 7 was observed.