1,5-Di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose | 123212-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,5-Di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose
• 英文别名: 1,5-di-O-acetyl-3-phthalimido-2,3-dideoxy-β-D-erythro-pentafuranose；[(2S,3S,5S)-5-acetyloxy-3-(1,3-dioxoisoindol-2-yl)oxolan-2-yl]methyl acetate
• CAS: 123212-51-1
• 化学式: C₁₇H₁₇NO₇
• 分子量: 347.324
• InChiKey: HWXVFWMHTLZBTM-RRFJBIMHSA-N

物化性质

• 熔点：
  154-156 °C
• 沸点：
  476.0±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-Di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose 在 三氟甲磺酸三甲基硅酯 甲胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 4.5h， 生成 3'-氨基-2',3'-双脱氧胸苷
  参考文献：
  名称：

  A Convenient Route to 3′-Amino-3′-deoxythymidine

  摘要：

  据报道，标题化合物9及其α-异构体10的合成过程高效且便捷。因此，在40°C下，在CHCl3中使用P4O10/H2O/n-Bu3N试剂，将邻苯二甲酰亚胺与未保护的2-脱氧-D-核糖（1）直接缩合，然后进行乙酰化，得到二-O-乙酰基-邻苯二甲酰亚胺衍生物2和3，这些衍生物也可以通过DBU邻苯二甲酰亚胺盐与4-乙酰氧基-5-羟基-2-戊烯醛5的反应来合成。2与硅化胸腺嘧啶的反应，使用路易斯酸三甲基硅基三氟甲磺酸盐作为催化剂，得到化合物7和8，通过分馏结晶分离，并用33%的甲胺/乙醇处理脱保护，分别得到相应的3-氨基核苷9和10。

  DOI：

  10.1055/s-1989-27259
• 作为产物：
  描述：

  (2E)-4-O-acetyl-2,3-dideoxy-aldehyde-D-pent-2-enose 、 isoindole-1,3-dione;2,3,4,5,7,8,9,10-octahydropyrido[1,2-a][1,3]diazepine 生成 1,5-Di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose
  参考文献：
  名称：

  PEDERSEN, ERIK B.;MOTAWIA, MOHAMMED S.;ANDREASSEN, ERIK S.;WENGEL, JESPER+, NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 1069-1070

  摘要：

  DOI：

文献信息

• Synthesis of 3′-(4-Nitroimidazol-1-yl)-2′,3′-dideoxynucleosides of Pyrimidine Analogues and their Biological Evaluation against HIV
  作者：Mohammed S. Motawia、Erik B. Pedersen、Jerzy Suwinski、Carsten M. Nielsen

  DOI：10.1002/ardp.19903231203

  日期：——

  1,5‐di‐O‐acetyl‐2,3‐dideoxy‐3‐phthalimido‐β‐D‐erythro‐pentofuranose (1) with silylated pyrimidinediones 2a–c using the Lewis acid trimethylsilyl triflate as catalyst afforded nucleosides 3a–c and 4a,c which were deprotected with 33% methylamine/ethanol to give the corresponding 3‐aminonucleosides 5a–c and 6. These were reacted with 1,4‐dinitroimidazoles 7a,b to give the 3‐imidazolyldideoxynucleosides

  1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose (1) 与甲硅烷基化嘧啶二酮 2a – c 使用路易斯酸三甲基甲硅烷基三氟甲磺酸酯作为催化剂反应得到核苷 3a– c 和 4a、c 用 33% 甲胺/乙醇脱保护得到相应的 3-氨基核苷 5a-c 和 6。这些与 1,4-二硝基咪唑 7a、b 反应得到 3-咪唑基二脱氧核苷 8a、b 和 9a -F。在亚毒性浓度下，这些化合物对 HIV-1 无效。
• 2’-Deoxypuromycin: Synthesis and Antiviral Evaluation
  作者：Mohammed S. Motawia、Morten Meldal、Mamdouh Sofan、Paul Stein、Erik B. Pedersen、Claus Nielsen

  DOI：10.1055/s-1995-3892

  日期：1995.3

  A new synthesis of 2’-deoxypuromycin (18) as well as its α-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifluoromethanesulfonate as catalyst afforded the α and β nucleosides 7 and 12 in 15 and 25% yield, respectively. After deblocking of both amino and hydroxy groups with methylamine in ethanol, the nucleosides were condensed with Fmoc-4-O-methyl-L-tyrosine and subsequently deprotected to give the target compounds 17 and 18. Compound 3 is converted into its glycosyl bromide 4 in quantitative yield on treatment with trimethylsilyl bromide, and reacted with the sodium salt of 6-dimethylaminopurine to give the corresponding protected N-7 and N-9 α glycosyl nucleosides 7 and 8 in 34 and 39% yield, respectively. The 2’-deoxypuromycin is inactive against HIV-1 in MT-4 cells.

  本文描述了 2'-deoxypuromycin (18) 及其 δ-anomer 17 的新合成方法。以三氟甲磺酸三甲基硅酯为催化剂，将 1,5-二-O-乙酰基-2,3-二脱氧-3-邻苯二甲酰亚氨基-δ-D-赤式戊呋喃糖 (3) 与硅烷化的 6-二甲基氨基嘌呤反应，得到了δ和δ核苷 7 和 12，产率分别为 15% 和 25%。在乙醇中用甲胺脱锁氨基和羟基后，核苷与 Fmoc-4-O-methyl-L-tyrosine 缩合，随后脱保护，得到目标化合物 17 和 18。化合物 3 经三甲硅基溴化物处理后定量转化为其糖基溴化物 4，并与 6-二甲氨基嘌呤钠盐反应，得到相应的受保护 N-7 和 N-9 δ糖基核苷 7 和 8，收率分别为 34% 和 39%。2'-deoxypuromycin 对 MT-4 细胞中的 HIV-1 无活性。
• Synthesis of 5-Alkoxymethyl Derivatives of 3'-Amino-2',3'-dideoxyuridine and Evaluation of their Activity against HIV and Cancer.
  作者：Mohammed S. Motawia、Ahmed E. S. Abdel-Megied、Erik B. Pedersen、Carsten M. Nielsen、Peter Ebbesen、Daniel R. Carcanague、Ito Chao、K. N. Houk

  DOI：10.3891/acta.chem.scand.46-0077

  日期：——

  3-dideoxy-beta- D-erythro-pentofuranose (3), in the presence of trimethylsilyl triflate as a catalyst, to give the corresponding 3'-phthalimido-2',3'-dideoxynucleosides 5a-f and 6 which on treatment with 33% methylamine-ethanol afforded the corresponding 3'-amino-2',3'-dideoxynucleosides 7a-f and 8 in high yields. Compound 7d showed colony inhibition when tested against human epidermoid cervical cancer cells

  5-烷氧基甲基尿嘧啶2a-c已通过5-羟基甲基尿嘧啶（1）的酸催化醚化反应制备。将化合物1、2a-c，5-甲氧基甲基-和5-苄氧基甲基-尿嘧啶甲硅烷基化并与1,5-二-O-乙酰基-3-邻苯二甲酰亚胺基-2,3-二脱氧-β-D-赤型戊呋喃糖（ 3），在三氟甲磺酸三甲基甲硅烷基酯作为催化剂的存在下，得到相应的3'-邻苯二甲酰亚胺基-2'，3'-二脱氧核苷5a-f和6，将其用33％甲胺-乙醇处理后得到相应的3'-氨基-2'，3'-二脱氧核苷7a-f和8的产量很高。当针对人表皮样宫颈癌细胞进行测试时，化合物7d显示出集落抑制作用。核苷5a-e，7a-f和8没有显示出对HIV-1的任何显着活性。
• Synthesis of 3?-deoxy-3?-fluoro and -3?-amino nucleosides from 2-methylthiopyrimidin-4(1H)-ones
  作者：M. A. Zahran、A. E. -S. Abdel-Megied、A. A. -H. Abdel-Rahman、M. A. Sofan、C. Nielsen、E. B. Pedersen

  DOI：10.1007/bf00807039

  日期：——

  Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-beta-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-beta-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones 2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides 5, 6, 13. In these reactions, an endocyclic cleavage of C-O in 3 took place; therefore, acyclic nucleosides 4a,b were also formed. All 3'-fluoro nucleosides were deprotected with NH3/MeOH; the 3'-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3'-deoxy-3'-fluorothylmidine showed moderate activity against HIV-1.
• El-Barbary, Ahmed A.; El-Brollosy, Nasser R.; Pedersen, Erik B., Heterocycles, 1994, vol. 38, # 10, p. 2191 - 2198
  作者：El-Barbary, Ahmed A.、El-Brollosy, Nasser R.、Pedersen, Erik B.

  DOI：——

  日期：——