CAS: 141846-57-3; (2S,3R,5R)-5-Chloro-2-(((4-Methylbenzoyl)Oxy)Methyl)Tetrahydrofuran-3-Yl 4-Methylbenzoate
该化合物是一种合成有机化合物,其特点是五人组成的含氧环,其成分为五人制糖糖结构.该化合物具有氯化替代成分,表明其在核循环替代反应中具有潜在的再活动性.两个四甲基苯甲酸酯群体的存在表明,它可能具有疏水特性,从而影响其溶解性以及与生物膜的相互作用.2-dexyl配置表明,第二碳中缺少一种氢氧基化合物,这在生物环境,特别是在核核循环化学方面意义重大.该化合物可能具有对药用化学和生物化学的兴趣,特别是它有可能在核循环模拟合成中或作为发展胶合化合物的建筑块.其具体的再活性和稳定性将取决于周围的条件,例如pH和溶剂,因此它成为进一步进行化学修改的灵活候选条件.
- 英文名称(2S,3R,5R)-5-Chloro-2-(((4-Methylbenzoyl)Oxy)Methyl)Tetrahydrofuran-3-Yl 4-Methylbenzoate
- 中文名称1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-L-呋喃核糖
- IUPAC名称(2S,3R,5R)-5-chloro-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
- 其它别名Alpha-L-Erythro-Pentofuranosyl Chloride-2-Deoxy-Bis(4-Methyl Benzoate); 1-Chloro-3,5-Di-O-Toluoyl-2-Deoxy-L-Ribofuranose; 1-Chloro-2-Deoxy-3,5-Di-O-Toluoyl-L-Ribose; 2-Deoxy-3,5-Di-O-P-Toluoyl-α-L-Ribofuranosyl Chloride; Chloro-3,5-Di-O-Toluoyl-2-Deoxy-α-L-Ribofuranose; Telbivudine Impurity 3; 1-Chloro-2-Deoxy-3,5-Di-O-Toluoyl-L-Ribofuranose; 2-Deoxy-3,5-Di-O-P-Toluoyl-A-L-Ribofuranosyl Chloride
- CAS编号141846-57-3
- MFCD编号:MFCD09037391
- EINECS号:604-255-4
- 分子式:C21H21ClO5
- 分子量:388.85
- 产品CID: 641034
- 产品分类生物化工 → 糖类化合物 → 单糖
物理性质
MSDS等安全信息
上下游产品
methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose D-2-deoxyribose 1-O-methyl-2-deoxy-D-ribofuranoside 4-methyl-benzoyl chloride D-erythro-1,2-dideoxy-pentofuranose1-(2,6-bis-benzyloxy-pyridin-3-yl)-ξ-D-erythro-1,2-dideoxy-pentofuranose 2,5-anhydro-3-deoxy-4,6-di-O-toluoyl-D-ribohexononitrile 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranosyl 1-cyanide 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one合成工艺路线路线简述
- 合成目标产物 Alpha-L-Erythro-Pentofuranosyl Chloride-2-Deoxy-Bis(4-Methyl Benzoate) 主要起始原料 L-Erythro-Pentofuranoside, Methyl 2-Deoxy-, 3,5-Bis(4-Methylbenzoate)
- (文献来源)合成步骤主要原料 L-Erythro-Pentofuranoside, Methyl 2-Deoxy-, 3,5-Bis(4-Methylbenzoate)
D-吡喃木糖置于吡啶,氢溴酸,二异丁基氢化铝,Potassium Carbonate,溶剂黄146,三氟乙酸,Sodium Iodide,Potassium Hydroxide体系中,用 乙二醇二甲醚,正己烷,甲基叔丁基醚,醋酸异丙酯,水,溶剂黄146 用作溶剂,化学反应 20.66H,反应生成1-氯-2-脱氧-3,5-二-O-对甲苯甲酰基-L-呋喃核糖
参考文献:Development Of A Novel Synthetic Process For 2-Deoxy-3,5-Di-O-P-Toluoyl-α-L-Ribofuranosyl Chloride: A Versatile Intermediate In The Synthesis Of 2'-Deoxy-L-Ribonucleosides
标题:Development Of A Novel Synthetic Process For 2-Deoxy-3,5-Di-O-P-Toluoyl-α-L-Ribofuranosyl Chloride: A Versatile Intermediate In The Synthesis Of 2'-Deoxy-L-Ribonucleosides
摘要:A Novel Synthetic Route To 2-Deoxy-3,5-Di-O-P-Toluoyl-Alpha-L-Ribofuranosyl Chloride (1) From Inexpensive D-Xylose (3) Is Described. 1 Is A Key Intermediate In The Synthesis Of The Antiviral Agent 1-(2-Deoxy-Beta-L-Ribofuranosyl)Thymine (Beta-L-Thymidine) (2) And Other 2'-Deoxy-L-Ribonucleosides. This Seven-Step Synthesis Employs A Key Conversion Of The D To The L Configuration Of The Sugar Moiety (6 To 7 In Scheme 1) Using Simple Reagents And Reaction Conditions. The Entire Process Involves Only Three Isolation Steps. The Key Compound (1) Was Produced In 11% Overall Yield Without Chromatography.
Doi:10.1021/op0500436
海关参考信息
- 2905122000-异丙醇
2905310000-1,2-乙二醇
2905320000-1,2-丙二醇
2905399001-1,3-丙二醇 - 💡 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。
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专利信息
专利号:EP-1600451-A2
优先权日:1999-11-12
标题 :Synthesis of 2'-deoxy-l-nucleosides
专利号:EP-1639121-A4
优先权日:2003-06-30
标题:SYNTHESIS OF BETA-L-2-DESOXYNUCLEOSIDES
专利号:EP-1600452-A2
优先权日:1999-11-12
标题 :Synthesis of 2'-deoxy-L-nucleosides
专利号:EP-1634888-A2
优先权日:1999-11-12
标题 :Synthesis of 2'-deoxy-L-nucleosides
专利号:US-2005059632-A1
优先权日:2003-06-30
标题 :Synthesis of beta-L-2'-deoxy nucleosides
专利号:WO-2005003374-A2
优先权日:2003-06-30
标题 :SYNTHESIS OF β-L-2-DEOXY NUCLEOSIDES
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141846-57-3
(2S,3R,5R)-5-Chloro-2-(((4-methylbenzoyl)oxy)-methyl)tetrahydrofuran-3-yl 4-methylbenzoate
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主要参考文献
参考标题:Synthesis Of Beta-L-2'-Deoxy Nucleosides摘要:An Improved Process For The Preparation Of 2′-Modified Nucleosides And 2′-Deoxy-Nucleosides, Such As, β-L-2′-Deoxy-Thymidine (Ldt), Is Provided. In Particular, The Improved Process Is Directed To The Synthesis Of A 2′-Deoxynucleoside That May Utilize Different Starting Materials But That Proceeds Via A Chloro-Sugar Intermediate Or Via A 2,2′-Anhydro-1-Furanosyl-Nucleobase Intermediate. Where An 2,2′-Anhydro- 1 -Furanosyl Base Intermediate Is Utilized, A Reducing Agent, Such As Red-Al, And A Sequestering Agent, Such As 15-Crown-5 Ether, That Cause An Intramolecular Displacement Reaction And Formation Of The Desired Nucleoside Product In Good Yields Are Employed. An Alternative Process Of The Present Invention Utilizes A 2,2′-Anhydro-1-Furanosyl Base Intermediate Without A Sequestering Agent To Afford 2′-Deoxynucleosides In Good Yields. The Compounds Made According To The Present Invention May Be Used As Intermediates In The Preparation Of Other Nucleoside Analogues, Or May Be Used Directly As Antiviral And/or Antineoplastic Agents.
合成参考文献
参考DOI号:10.1080/07328319908044612
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