Tetramethyltin → 1,6-anhydro-3,4-dideoxy-3-methyl-beta-D-glycero-hex-3-enopyranos-2-ulose

HRID 1769236노트

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HRID 1769236 반응식
C[Sn](C)(C)C.[CH3:6]N1CCCC1=O.I[C:14]1[C:15](=[O:22])[C@@H:16]2[O:21][CH2:20][C@H:18]([CH:19]=1)[O:17]2.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cu]I.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C>[CH3:6][C:14]1[C:15](=[O:22])[C@@H:16]2[O:21][CH2:20][C@H:18]([CH:19]=1)[O:17]2

참가 물질

8

반응물 4

HCID 11661TetramethyltinHCID 11773TriphenylarsineHCID 13387N-methyl-2-pyrrolidoneHCID 80272516,8-Dioxabicyclo[3.2.1]oct-2-en-4-one, 3-iodo-, (1S,5R)-

생성물 1

HCID 701307781,6-anhydro-3,4-dideoxy-3-methyl-beta-D-glycero-hex-3-enopyranos-2-ulose

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 498840Bis(benzonitrile)palladium chloride촉매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

5.3 g of tetramethyltin was added to 20 ml of a dry N-methylpyrrolidinone solution containing a mixture comprising 5 g of 1,6-anhydro-3,4-dideoxy-3-iodo-β-D-glycero-hex-3-enopyranos-2-ulose, 0.4 g of copper(I) iodide, 0.6 g of triphenylarsine and 0.4 g of dichlorobis(benzonitrile)palladium(II) under an inert atmosphere of nitrogen gas. The mixture was stirred at 80° C. for 4 hours. Then, 200 ml of ethyl acetate was added thereto, and the mixture was washed three times with 100 ml of a 10% potassium fluoride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained syrup product was purified by silica gel column chromatography (ethyl acetate: hexane=1:3) and then distilled under reduced pressure to obtain 1.61 g of the desired product (Intermediate No. 2) as a colorless transparent liquid. The NMR analytical data of this product are as follows.

후처리

  1. washthe mixture was washed three times with 100 ml of a 10% potassium fluoride aqueous solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained syrup product was purified by silica gel column chromatography (ethyl acetate: hexane=1:3)
  5. distillationdistilled under reduced pressure

출처 및 근거

ORD 기록
ord-c715a54ebc0342aeb4d04ff8f7b30de9
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380834

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