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Citric Acid → 1-(beta-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienyl-methyl)-4-methylbenzene

HRID 1625729
ノート
印刷プレビュー

反応式

HRID 1625729 の反応式
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]2[S:33][C:34]([C:37]3[CH:38]=[N:39][C:40]([F:43])=[CH:41][CH:42]=3)=[CH:35][CH:36]=2)[CH:25]=1)(=O)C.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1.O1CCCC1>[C@@H:6]1([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]3[S:33][C:34]([C:37]4[CH:38]=[N:39][C:40]([F:43])=[CH:41][CH:42]=4)=[CH:35][CH:36]=3)[CH:25]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]
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 311Citric AcidHCID 14798Sodium HydroxideHCID 666084961-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene

生成物 1

HCID 529174341-(beta-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienyl-methyl)-4-methylbenzene収率 120.1%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 312751,4-Dioxane溶媒

実験手順

The above 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene 59 (39 mg) was dissolved in 1,4-dioxane (4 ml)-tetrahydrofuran (4 ml), and added thereto was 2N sodium hydroxide (2 ml). The mixture was stirred at room temperature for one hour. The mixture was made acidic by addition of an aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the desired 1-(β-D-glucopyranosyl)-3-(5-(6-fluoro-3-pyridyl)-2-thienylmethyl)-4-methylbenzene 60 (34 mg) as colorless powder. APCI-Mass m/Z 463 (M+NH4).

後処理

  1. additionadded
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-f6c99cacff794b729abb53dc4a611b9c
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785403B2

反応ノート

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