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

HRID 1769236ノート

反応式

HRID 1769236 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 498840Bis(benzonitrile)palladium chloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c715a54ebc0342aeb4d04ff8f7b30de9
出典データセット
uspto-grants-1995_01
特許番号
US05380834

反応ノート

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