2,5-anhydro-1-azido-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate | 161855-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2,5-anhydro-1-azido-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate
• 英文别名: S-[(2R,3R)-2-(azidomethyl)oxolan-3-yl] ethanethioate
• CAS: 161855-47-6
• 化学式: C₇H₁₁N₃O₂S
• 分子量: 201.249
• InChiKey: PNPARUANGKXWPK-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-1-azido-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (4R,5S,6S)-3-((2R,3R)-2-Azidomethyl-tetrahydro-furan-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel THF 1β-methylcarbapenems

  摘要：

  A series of twelve highly active aminomethyl-THF 1 beta-methylcarbapenems 3a-1 were synthesized. Of these, carbapenems 3a-f demonstrated a spectrum of antimicrobial activity comparable to those of imipenem and meropenem with the exception of only moderate anti-pseudomonal activity. Most importantly, they demonstrated moderate intrinsic oral activity against an E. coli infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00282-5
• 作为产物：
  描述：

  1,2-二脱氧-D-核糖 在 吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2,5-anhydro-1-azido-1,4-dideoxy-3-thio-D-threo-pentitol 3-acetate
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel THF 1β-methylcarbapenems

  摘要：

  A series of twelve highly active aminomethyl-THF 1 beta-methylcarbapenems 3a-1 were synthesized. Of these, carbapenems 3a-f demonstrated a spectrum of antimicrobial activity comparable to those of imipenem and meropenem with the exception of only moderate anti-pseudomonal activity. Most importantly, they demonstrated moderate intrinsic oral activity against an E. coli infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00282-5

文献信息

• Convergent Syntheses of Oral THF 1.BETA.-Methylcarbapenems.
  作者：PANAYOTA BITHA、ZHONG LI、YANG-I LIN

  DOI：10.7164/antibiotics.52.643

  日期：——

  Convergent syntheses of oral THF 1beta-methylcarbapenems 4 (OCA-983) and 5 starting from M2-phosphate 1 were developed. Reaction of the M2-phosphate 1 with THF thiols containing a requisite prodrug side chain, 9 and 10, gave the desired oral THF 1beta-methylcarbapenems 4 and 5, respectively, in 46% and 42% overall yields.

  从M2-磷酸酯1开始开发了口服THF1β-甲基卡巴培南4（OCA-983）和5的聚合合成方法。M2-磷酸酯1与含有必需的前药侧链9和10的THF硫醇反应，分别以46％和42％的总收率得到所需的口服THF1β-甲基咔ap烯4和5。
• 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.
• Synthesis and structure-activity relationships of novel THF 1β-methylcarbapenems
  作者：Yang-I Lin、Panayota Bitha、Subas M. Sakya、Timothy W. Strohmeyer、Zhong Li、Ving J. Lee、Stanley A. Lang、Youjun Yang、Niraja Bhachech、William J. Weiss、Peter J. Petersen、Nilda V. Jacobus、Karen Bush、Raymond T. Testa、Francis P. Tally

  DOI：10.1016/s0960-894x(97)00282-5

  日期：1997.7

  A series of twelve highly active aminomethyl-THF 1 beta-methylcarbapenems 3a-1 were synthesized. Of these, carbapenems 3a-f demonstrated a spectrum of antimicrobial activity comparable to those of imipenem and meropenem with the exception of only moderate anti-pseudomonal activity. Most importantly, they demonstrated moderate intrinsic oral activity against an E. coli infection in mice. (C) 1997 Elsevier Science Ltd.