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Triethylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-(2-acetoxyethyl)thioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 1854252
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HRID 1854252 반응식
[C:1]([O:4][C@H:5]1[C@H:10]([N:11]=[C:12]=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[C:34]([O:37][CH2:38][CH2:39][NH2:40])(=[O:36])[CH3:35].C(N(CC)CC)C>CC#N.C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([NH:11][C:12]([NH:40][CH2:39][CH2:38][O:37][C:34](=[O:36])[CH3:35])=[S:13])[C@@H:9]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:18][C:19](=[O:21])[CH3:20])[C@@H:7]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[O:6]1)(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 14130735(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetateHCID 873085332-aminoethyl acetate TFA-salt

생성물 1

HCID 87308604(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-(2-acetoxyethyl)thioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate수율 92%

시약·촉매·용매 2

HCID 6342
Acetonitrile
용매
HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (500 mg, 1.3 mmol) in CH3CN (10 mL) was added 2-aminoethyl acetate trifluoroacetate (600 mg, 3 mmol) and triethylamine (0.5 mL, 3.5 mmol). The mixture was stirred at room temperature for 1 h. The solution was diluted with CH2Cl2 (50 mL) and washed with saturated aqueous NaHCO3 (20 mL), and the organic extract was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on silica gel (hexane/EtOAc 1:1) to give (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-(2-acetoxyethyl)thioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white foam (580 mg, 92% yield). 1H NMR (600 MHz, DMSO-d6) δ 2.06 (s, 3H), 2.08 (s, 3H), 2.11 (s, 3H), 2.12 (s, 3H), 2.15 (s, 3H), 3.66-3.80 (m, 2H), 3.85 (ddd, 1H, J=2.5, 4.5, 9.0 Hz), 4.14 (dd, 1H, J=2.0, 12.5 Hz), 4.22 (dd, 1H, J=5.0, 5.0 Hz), 4.29 (dd, 1H, J=4.5, 12.5 Hz), 4.65-4.75 (m, 1H), 5.13-5.22 (m, 2H), 5.73 (d, 1H, J=8.5 Hz).13C NMR (125 MHz, DMSO-d6) δ 20.82, 20.86, 20.98, 21.04, 21.19, 40.51, 57.21, 61.85, 62.75, 68.25, 71.84, 73.12, 92.65, 169.34, 169.73, 170.13, 170.49, 170.77, 184.26.

후처리

  1. washwashed with saturated aqueous NaHCO3 (20 mL)
  2. extractionthe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel (hexane/EtOAc 1:1)

출처 및 근거

ORD 기록
ord-58dd4605a8294152ba48276b85944880
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962664B2

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