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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
ノート
印刷プレビュー

反応式

HRID 1854252 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342
Acetonitrile
溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-58dd4605a8294152ba48276b85944880
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962664B2

反応ノート

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