CAS: 865363-93-5; (2R,3S,5R)-5-(6-Amino-2-Fluoro-9H-Purin-9-yl)-2-Ethynyl-2-(Hydroxymethyl)Tetrahydrofuran-3-Ol

• 英文名称(2R,3S,5R)-5-(6-Amino-2-Fluoro-9H-Purin-9-yl)-2-Ethynyl-2-(Hydroxymethyl)Tetrahydrofuran-3-Ol
• 中文名称2'-脱氧-4'-C-乙炔基-2-氟腺苷
• IUPAC名称Islatravir
• 其它别名Efda; 4'-E-D2-Fa; (2R,3S,5R)-5-(6-Amino-2-Fluoropurin-9-yl)-2-Ethynyl-2-(Hydroxymethyl)Oxolan-3-Ol; Adenosine, 2'-Deoxy-4'-C-Ethynyl-2-Fluoro-; 1,4-Bis-Aminomethylbenzen [czech]; Islatravir [usan]
• CAS编号865363-93-5
• MFCD编号:MFCD28502143
• EINECS号:858-586-6
• FDA UNII编号:QPQ082R25D
• 分子式:C12H12FN5O3
• 分子量:293.26
• 产品CID: 1867720
• 同类组份化合物CAS2408129-39-3 (hydrate)865363-93-5 (free base)
• 产品分类有机原料 → 有机杂环化合物 → 咪唑并嘧啶类

• 相似结构搜索
• InChIKey: IKKXOSBHLYMWAE-QRPMWFLTSA-N
• InChI=1S/C12H12FN5O3/c1-2-12(4-19)6(20)3-7(21-12)18-5-15-8-9(14)16-11(13)17-10(8)18/h1,5-7,19-20H,3-4H2,(H2,14,16,17)/t6-,7+,12+/m0/s1…
• 计算化学: 氢键受体数8.0氢键供体数3.0可旋转键数3.0

物理性质

• 熔点220.0-221.4 °C (分解)
• 沸点669.2±65.0 °C(预测)
• 密度1.72±0.1 g/cm3(预测)
• pKa:13.11±0.60(预测)
• PSA:119.31
• LogP:-0.2271
• 溶解性DMSO:100.0(Max Conc. mg/mL);341.0(Max Conc. Mm) Water:3.57(Max Conc. mg/mL);12.17(Max Conc. Mm)
• 外观形态白色至类白色固体
• 储存条件储存在 -20°C
• 产品应用该化合物用于治疗艾滋病毒.

MSDS等安全信息

• GHS象形图
• GHS符号GHS06 & GHS08;
  注释: Skull and crossbones & Health hazard
• 危险类别急性毒性 类别3(经口)
  STOT SE 2
  特定目标器官毒性-重复接触 类别2
• 警示词Danger(危险)
• 危险描述H301 |吞咽会中毒.
  H371 |可能损害器官.
  H373 |长期或反复接触可能损害器官.
• 防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338

欧盟法规

上下游产品

合成工艺路线路线简述

• 700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: Potassium Hydroxide Catalysts: Phosphoribomutase,Purine Nucleoside Phosphorylase Solvents: Water; Ph 6.94 - 7.5,Rt -> 40 °C; 24 H,40 °C
  标题:Nine-Step Stereoselective Synthesis Of Islatravir From Deoxyribose
  作者:Nawrat,Christopher C.; Et Al
  参考文献:Organic Letters 日期:2020 卷标:22(6) 页码:2167-2172]
  
  700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: Sucrose,Triethanolamine,Potassium Hydroxide Catalysts: Manganese Dichloride Solvents: Water; Ph 7.56,20 °C1.2 Reagents: Potassium Hydroxide Solvents: Water; Ph 7.45 - 7.59,20 °C1.3 Reagents: Potassium Hydroxide Solvents: Isopropanol; Ph 7.48 - 7.58,20 °C1.4 Catalysts: Fructose Bisphosphate Aldolase,Phosphoribomutase,Purine Nucleoside Phosphorylase,Sucrose Phosphorylase; 21 H,35 °C; 60 Min,35 °C -> 5 °C
  标题:Synthesis Of Islatravir Enabled By A Catalytic,Enantioselective Alkynylation Of A Ketone
  作者:Patel,Niki R.; Et Al
  参考文献:Organic Letters 日期:2020 卷标:22(12) 页码:4659-4664]
  
  700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: Triethanolamine,Potassium Hydroxide Solvents: Water; Ph 7.61.2 Reagents: Sucrose,Potassium Hydroxide,Manganese Dichloride Catalysts: Purine Nucleoside Phosphorylase,Sucrose Phosphorylase Solvents: Isopropanol; 26 H,Ph 7.5,35 °C
  标题:Five-Step Enantioselective Synthesis Of Islatravir Via Asymmetric Ketone Alkynylation And An Ozonolysis Cascade
  作者:Patel,Niki R.; Et Al
  参考文献:Chemistry - A European Journal 日期:2020 卷标:26(62) 页码:14118-14123]
  
  2072080-29-4 = 865363-93-5
  反应条件:1.1 Reagents: Sodium Methoxide Solvents: Methanol,Tetrahydrofuran; 0 °C; Overnight,Rt1.2 Reagents: Acetic Acid; 1 H,Rt
  标题:Enantioselective Synthesis Of 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine (Efda) Via Enzymatic De-Symmetrization
  作者:Mclaughlin,Mark; Et Al
  参考文献:Organic Letters 日期:2017 卷标:19(4) 页码:926-929]
  
  1332623-07-0 = 865363-93-5 [标题:Reaction Conditions
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  1646857-60-4 = 865363-93-5
  反应条件:1.1 Reagents: Lithium,Ammonia
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  1646857-59-1 = 865363-93-5
  反应条件:1.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 30 Min,Rt1.2 Reagents: Sodium,Ammonia Solvents: Tetrahydrofuran; 10 Min,-78 °C1.3 Reagents: Ammonium Chloride Solvents: Water; 0 °C; 0 °C -> Rt; 1 H,Rt
  标题:Synthesis Of Efda Via A Diastereoselective Aldol Reaction Of A Protected 3-Keto Furanose
  作者:Fukuyama,Kei; Et Al
  参考文献:Organic Letters 日期:2015 卷标:17(4) 页码:828-831]
  
  = 865363-93-5
  反应条件:1.1 Reagents: Cerium Ammonium Nitrate Solvents: Acetonitrile,Water; 3 H,0 °C
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  1646857-56-8 = 865363-93-5
  反应条件:1.1 -2.1 Reagents: Lithium,Ammonia
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  2072080-29-4 = 865363-93-5 [标题:Reaction Conditions
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  1332623-00-3 + 1332623-07-0 = 865363-93-5
  反应条件:1.1 Reagents: Ammonium Fluoride Solvents: Methanol,Dichloromethane; 16 H,Rt1.2 Reagents: Methanol; 27 H,Rt1.3 Reagents: Ammonia Solvents: Methanol; Ph 101.4 Reagents: Dowex 50W; Ph 41.5 Reagents: Calcium Carbonate; 30 Min
  标题:Concise Synthesis Of The Anti-Hiv Nucleoside Efda
  作者:Kageyama,Masayuki; Et Al
  参考文献:Bioscience 日期:2012 卷标:76(6) 页码:1219-1225]
  
  1332623-07-0 = 865363-93-5
  反应条件:1.1 Reagents: Ammonium Fluoride Solvents: Methanol,Dichloromethane; 16 H,Rt1.2 Solvents: Methanol; 27 H,Rt1.3 Reagents: Sodium Hydroxide Solvents: Methanol; Ph 10,Rt; 10 Min,Rt1.4 Reagents: Dowex 50W; Ph 4,Rt1.5 Reagents: Calcium Carbonate; 30 Min,Rt
  标题:Enantioselective Total Synthesis Of The Potent Anti-Hiv Nucleoside Efda
  作者:Kageyama,Masayuki; Et Al
  参考文献:Organic Letters 日期:2011 卷标:13(19) 页码:5264-5266]
  
  933791-14-1 + 700-49-2 = 865363-93-5
  反应条件:1.1 Catalysts: 5′-Atp,Pantothenate Kinase,Acetate Kinase1.2 Catalysts: Catalase,Peroxidase,Galactose Oxidase1.3 Catalysts: 2-Deoxyribose 5-Phosphate Aldolase1.4 Catalysts: Phosphoribomutase,Purine Nucleoside Phosphorylase,Sucrose Phosphorylase
  标题:Development And Validation Of Ion-Pairing Hplc-Cad Chromatography For Measurement Of Islatravir'S Phosphorylated Intermediates
  作者:Gunsch,Matthew J.; Et Al
  参考文献:Journal Of Pharmaceutical And Biomedical Analysis 日期:2022 卷标:213]
  
  10416-59-8 + 700-49-2 + 2072080-28-3 = 865363-93-5
  反应条件:1.1 Solvents: Acetonitrile; 1 H,70 °C; 70 °C -> Rt1.2 Reagents: Trimethylsilyl Triflate; Rt; Rt -> 70 °C1.3 Solvents: Acetonitrile,Toluene; 1 H,70 °C2.1 Reagents: Sodium Methoxide Solvents: Methanol,Tetrahydrofuran; 0 °C; Overnight,Rt2.2 Reagents: Acetic Acid; 1 H,Rt
  标题:Enantioselective Synthesis Of 4'-Ethynyl-2-Fluoro-2'-Deoxyadenosine (Efda) Via Enzymatic De-Symmetrization
  作者:Mclaughlin,Mark; Et Al
  参考文献:Organic Letters 日期:2017 卷标:19(4) 页码:926-929]
  
  1332623-06-9 + 700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: N,O-Bis(Trimethylsilyl)Acetamide,Trimethylsilyl Triflate2.1 -
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227]
  
  1332623-06-9 + 700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: N,O-Bis(Trimethylsilyl)Acetamide Solvents: Acetonitrile; Rt; 2.5 H,Reflux; Reflux -> 0 °C1.2 Reagents: Trimethylsilyl Triflate; 15 Min,Rt; 17 H,Reflux1.3 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Ammonium Fluoride Solvents: Methanol,Dichloromethane; 16 H,Rt2.2 Reagents: Methanol; 27 H,Rt2.3 Reagents: Ammonia Solvents: Methanol; Ph 102.4 Reagents: Dowex 50W; Ph 42.5 Reagents: Calcium Carbonate; 30 Min
  标题:Concise Synthesis Of The Anti-Hiv Nucleoside Efda
  作者:Kageyama,Masayuki; Et Al
  参考文献:Bioscience 日期:2012 卷标:76(6) 页码:1219-1225]
  
  1332623-06-9 + 700-49-2 = 865363-93-5
  反应条件:1.1 Reagents: N,O-Bis(Trimethylsilyl)Acetamide Solvents: Acetonitrile; Rt; 2.5 H,Reflux; Reflux -> 0 °C1.2 Catalysts: Trimethylsilyl Triflate; 0 °C; 15 Min,Rt; 17 H,Reflux1.3 Reagents: Sodium Bicarbonate Solvents: Water; Reflux2.1 Reagents: Ammonium Fluoride Solvents: Methanol,Dichloromethane; 16 H,Rt2.2 Solvents: Methanol; 27 H,Rt2.3 Reagents: Sodium Hydroxide Solvents: Methanol; Ph 10,Rt; 10 Min,Rt2.4 Reagents: Dowex 50W; Ph 4,Rt2.5 Reagents: Calcium Carbonate; 30 Min,Rt
  标题:Enantioselective Total Synthesis Of The Potent Anti-Hiv Nucleoside Efda
  作者:Kageyama,Masayuki; Et Al
  参考文献:Organic Letters 日期:2011 卷标:13(19) 页码:5264-5266]
  
  1646857-56-8 = 865363-93-5
  反应条件:1.1 Reagents: Triethylamine Solvents: Methanol; Rt; 18 H,Reflux2.1 Reagents: Thiocarbonyldiimidazole Solvents: Toluene; 30 Min,Rt2.2 Reagents: Azobisisobutyronitrile,Tributylstannane Solvents: Toluene; 30 Min,Reflux3.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 30 Min,Rt3.2 Reagents: Sodium,Ammonia Solvents: Tetrahydrofuran; 10 Min,-78 °C3.3 Reagents: Ammonium Chloride Solvents: Water; 0 °C; 0 °C -> Rt; 1 H,Rt
  标题:Synthesis Of Efda Via A Diastereoselective Aldol Reaction Of A Protected 3-Keto Furanose
  作者:Fukuyama,Kei; Et Al
  参考文献:Organic Letters 日期:2015 卷标:17(4) 页码:828-831]
  
  1646857-57-9 = 865363-93-5
  反应条件:1.1 Reagents: Thiocarbonyldiimidazole Solvents: Toluene; 30 Min,Rt1.2 Reagents: Azobisisobutyronitrile,Tributylstannane Solvents: Toluene; 30 Min,Reflux2.1 Reagents: Tetrabutylammonium Fluoride Solvents: Tetrahydrofuran; 30 Min,Rt2.2 Reagents: Sodium,Ammonia Solvents: Tetrahydrofuran; 10 Min,-78 °C2.3 Reagents: Ammonium Chloride Solvents: Water; 0 °C; 0 °C -> Rt; 1 H,Rt
  标题:Synthesis Of Efda Via A Diastereoselective Aldol Reaction Of A Protected 3-Keto Furanose
  作者:Fukuyama,Kei; Et Al
  参考文献:Organic Letters 日期:2015 卷标:17(4) 页码:828-831]
  
  27607-77-8 + 700-49-2 + 2072080-28-3 = 865363-93-5
  反应条件:1.1 Reagents: N,O-Bis(Trimethylsilyl)Acetamide2.1 -
  标题:Synthesis Of Nucleotide Analogues,Efda,Eda And Edap,And The Effect Of Edap On Hepatitis B Virus Replication
  作者:Kamata,Mai; Et Al
  参考文献:Bioscience 日期:2020 卷标:84(2) 页码:217-227

海关参考信息

• 2901292000-乙炔
  2905122000-异丙醇
  2905143000-叔丁醇
  2905310000-1,2-乙二醇
• 💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
• 详情请参考：📖 海关编码查询和海关进出口税则

专利信息

其他信息查阅

• ➥ 象形图和危险代码
• ➥ 防范代码详解
• ➥ 危险代码说明
• ➥ Globally Harmonized System
• ➥ REACH监管