CAS: 77887-48-0; (N-Acetyl)-(4S)-Isopropyl-2-Oxazolidinone

英文名称(N-Acetyl)-(4S)-Isopropyl-2-Oxazolidinone
中文名称(N-乙酰基)-(4S)-异丙基-2-噁唑烷酮
IUPAC名称3-(2-methyl-3-oxobutan-2-yl)oxazolidin-2-one
其它别名N-Acetyl-(4S)-Isopropyl 2-Oxazolidinone; N-Acetyl-(4R)-Isopropyl 2-Oxazolidinone; (N-Acetyl)-(R)-4-Isopropyl-2-Oxazolidinone; (N-Acetyl)-(S)-4-Isopropyl-2-Oxazolidinone; 2-Oxazolidinone, 3-Acetyl-4-(1-Methylethyl)-, (4S)-; (4R)-3-Acetyl-4-Propan-2-Yl-2-Oxazolidinone; N-Acetyl-(4R)-Isopropyl 2-Oxazolidinone Usp/ep/bp; (4S)-3-Acetyl-4-Isopropyl-1,3-Oxazolidin-2-One
CAS编号77887-48-0
MFCD编号:MFCD00269652
分子式:C8H13NO3分子量:171.2
产品CID: 1773846
产品分类生物化工 → 多肽

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InChIKey: CBTGWPQJVPZGLZ-UHFFFAOYSA-N
InChI=1S/C8H13NO3/c1-6(10)8(2,3)9-4-5-12-7(9)11/h4-5H2,1-3H3
计算化学: 氢键受体数3.0氢键供体数*可旋转键数1.0

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合成工艺路线路线简述

📜L-缬氨酸置于三氟化硼乙醚正丁基锂,Dimethyl Sulfide Borane体系中,化学反应生成 (N-乙酰基)-(4S)-异丙基-2-噁唑烷酮
参考文献:Asymmetric Aldol Reactions. Use Of The Titanium Enolate Of A Chiral N-Acyloxazolidinone To Reverse Diastereofacial Selectivities
标题:Asymmetric Aldol Reactions. Use Of The Titanium Enolate Of A Chiral N-Acyloxazolidinone To Reverse Diastereofacial Selectivities
摘要:Aldol Reactions Of The Titanium Enolate Of (S)-N-Propionyl-4-Isopropyl-2-Oxazolidinone (Readily Derived From L-Valine) With Representative Aldehydes Give High Diastereofacial Selectivities For The Syn Aldol Adducts Expected From Chelation Control. This Represents A Remarkable Reversal In Selectivity Compared With The Corresponding Boron Enolate,Thus Permitting Either Enantiomeric Form Of Beta-Hydroxy-Alpha-Methyl Carboxylic Acids To Be Made From A Single,Readily Available Oxazolidinone Simply By Changing The Metal. A Lithium Interference Effect Is Shown To Be Easily Prevented By Use Of Excess Titanium. Use Of Diethyl Ether As Solvent Rather Than Thf Significantly Enhances The Stereoselectivity. Mechanistically,The Observed Stereochemical Reversal Constitutes Very Strong Evidence That Chelation Is Operative With Titanium,Presumably Through A Chelated Chairlike Transition Structure. In This Transition Structure,The Conformation Would Be Rigidly Locked By Chelation And The Titanium Would Be At Least Hexacoordinate,Resulting In A ''Superaxial'' Ligand,Thus Nicely Explaining The High Stereocontrol.
DOI:10.1021/jo00007A042