cis-4-(t-Butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane → cis 2-(Diethyloxyphosphinoyl)-4-hydroxymethyl-1,3-dithiolane

HRID 481717노트

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HRID 481717 반응식
[Si]([O:8][CH2:9][C@H:10]1[CH2:14][S:13][C@@H:12]([P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])[S:11]1)(C(C)(C)C)(C)C>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:18]([O:17][P:15]([O:20][CH2:21][CH3:22])([C@H:12]1[S:11][C@@H:10]([CH2:9][OH:8])[CH2:14][S:13]1)=[O:16])[CH3:19]

참가 물질

5

반응물 1

HCID 131720784cis-4-(t-Butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane

생성물 1

HCID 86752990cis 2-(Diethyloxyphosphinoyl)-4-hydroxymethyl-1,3-dithiolane수율 77.6%

시약·촉매·용매 3

HCID 6367Acetyl chloride촉매HCID 25517Ammonium Chloride촉매HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of cis-4-(t-butyldimethylsilyloxymethyl)-2-(diethyloxyphosphinoyl)-1,3-dithiolane (example 49) (3.70 g, 9.56 mmol) in anhydrous methanol (50 mL) was added acetyl chloride (6 drops) at 0° C. The solution was stirred at 0° C. for 30 min and then at room temperature for 4.5 hrs. A saturated solution of ammonium chloride (3 drops) was added and the solution was stirred for 15 min followed by evaporation of solvents. The crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (95:5) to give the compound (2.02 g) in 77% yield. 1H NMR (300 MHz, CDCl3) δ: 1.34 (t, 6H, J=7.0 Hz, CH3), 3.30 (dd, 1H, J=5.5 Hz, 12.0 Hz, H-5a), 3.42 (dd, 1H, J=6.0 Hz, 12.1 Hz, H-5b), 3.80 (m, 2H, CH2OH and 1H, OH), 4.05 (m, 1H, H-4) , 4.19 (m, 4H, CH2) , 4.35 (d, 1H, 2JHP =4.1 Hz, H-2).

후처리

  1. waitat room temperature for 4.5 hrs
  2. stirringthe solution was stirred for 15 min
  3. customfollowed by evaporation of solvents
  4. customThe crude material was purified by flash chromatography with a mixture of dichloromethane and methanol (95:5)

출처 및 근거

ORD 기록
ord-091340f044474edead9ae049ac6c895c
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789394

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