Potassium Carbonate → (2S,3R,4S,5S,6S)-2-((S)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1513210ノート

反応式

HRID 1513210 の反応式
[CH2:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([O:17][C@@H:18]([C:22]([O:35][CH3:36])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:19]([OH:21])=[O:20])[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:43]([O:46][C@@H:47]1[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:51]([O:57][C:58](=[O:60])[CH3:59])[C@@H:50]([C:61]([O:63][CH3:64])=[O:62])[O:49][C@@H:48]1Br)(=[O:45])[CH3:44]>C(#N)C>[C:43]([O:46][C@@H:47]1[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:51]([O:57][C:58](=[O:60])[CH3:59])[C@@H:50]([C:61]([O:63][CH3:64])=[O:62])[O:49][C@H:48]1[O:20][C:19](=[O:21])[C@@H:18]([O:17][C:12]1[N:11]=[C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:15]=[C:14]([CH3:16])[N:13]=1)[C:22]([O:35][CH3:36])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:45])[CH3:44]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 88785Acetobromo-alpha-D-glucuronic acid methyl esterHCID 59441453(s)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoic acid

生成物 1

HCID 59441455(2S,3R,4S,5S,6S)-2-((S)-2-(4-(Benzyloxymethyl)-6-methylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenylpropanoyloxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate収率 60.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of the compound of Example 14 (0.997 g, 2.05 mmol) in acetonitrile (20 mL) is added potassium carbonate (0.284 g, 2.05 mmol) and the reaction mixture stirred for 0.5 hr. (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (0.817 g, 2.05 mmol) is added to the reaction mixture and the reaction stirred for 12 hr. The reaction mixture is filtered and the filtrate concentrated under reduced pressure on a rotary evaporator to give a crude product. The crude product is purified by column chromatography on silica gel eluted with ethyl acetate-hexane (2:8) to yield the title compound (1.0 g, 60%). MS m/z 801.1 (M+.+1); 1H NMR (CDCl3, 200 MHz) δ 5.65 (C-6 pyran H, d, J5,6=8 Hz).

後処理

  1. stirringthe reaction stirred for 12 hr
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure on a rotary evaporator
  4. customto give a crude product
  5. customThe crude product is purified by column chromatography on silica gel
  6. washeluted with ethyl acetate-hexane (2:8)

出典と根拠

ORDレコード
ord-21fa2aab2d154a638430c3dca6ee25c8
出典データセット
uspto-grants-2012_07
特許番号
US08217155B2

反応ノート

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