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Butylamine → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-butylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 1854243
ノート
印刷プレビュー

反応式

HRID 1854243 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].[CH2:27]([NH2:31])[CH2:28][CH2:29][CH3:30].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:4][C@H:5]1[C@H:10]([NH:11][C:12]([NH:31][CH2:27][CH2:28][CH2:29][CH3:30])=[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

5

反応物 3

HCID 8007ButylamineHCID 516892Sodium BicarbonateHCID 14130735(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl triacetate

生成物 1

HCID 86638173(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-butylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate収率 97.1%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
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 (489 mg, 1.26 mmol) in CH2Cl2 (5 mL) was added neat butylamine (197 μL, 2.00 mmol) and the resulting mixture was stirred for 30 min. Saturated aqueous NaHCO3 (20 mL) was added, then the resulting mixture was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were dried (MgSO4) and concentrated. The resulting crude material was purified by flash chromatography on silica gel (hexane/EtOAc 1:1) to give (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-butylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white foam (566 mg, 97% yield). 1H NMR (500 MHz, CDCl3) δ 0.94 (t, 3H, J=7.5 Hz), 1.35-1.41 (m, 2H), 1.53-1.59 (m, 2H), 2.06 (s, 3H), 2.08 (s, 3H), 2.10 (s, 3H), 2.14 (s, 3H), 3.38 (br s, 2H), 3.82-3.85 (m, 1H), 4.13-4.16 (m, 2H), 4.20-4.25 (m, 1H), 4.29 (dd, 1H, J=4.5, 12.5 Hz), 5.17-5.22 (m, 2H), 5.73 (d, 1H, J=8.0 Hz), 6.10 (br s, 1H).

後処理

  1. extractionthe resulting mixture was extracted with CH2Cl2 (3×10 mL)
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting crude material was purified by flash chromatography on silica gel (hexane/EtOAc 1:1)

出典と根拠

ORDレコード
ord-90675c25f5024e289861ac35f1ab727e
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

読み込み中…

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