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Phenylacetic Acid → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-phenylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

HRID 2194647
ノート
印刷プレビュー

反応式

HRID 2194647 の反応式
Cl.[C:2]([O:5][C@H:6]1[C@H:11]([NH2:12])[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3].Cl.CN(C)CCCN=C=NCC.[C:38]1([CH2:44][C:45](O)=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:2]([O:5][C@H:6]1[C@H:11]([NH:12][C:45](=[O:46])[CH2:44][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:10]([O:13][C:14](=[O:16])[CH3:15])[C@H:9]([O:17][C:18](=[O:20])[CH3:19])[C@@H:8]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[O:7]1)(=[O:4])[CH3:3]
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 999Phenylacetic AcidHCID 2022591,3,4,6-Tetra-O-acetyl-a-D-glucosamineHCIHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 67206377(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-phenylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate収率 69%

試薬・触媒・溶媒 2

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-amino-tetrahydro-2H-pyran-2,4,5-triyl triacetate hydrochloride (0.500 g, 1.31 mmol) in CH2Cl2 (20 mL) was added 4-(dimethylamino)pyridine (0.478 g, 3.91 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.300 g, 1.57 mmol) and 2-phenylacetic acid (0.2132 g, 1.57 mmol). The reaction was stirred for 12 h. Additional CH2Cl2 (80 mL) was added and the organic layer was washed once with saturated aqueous NaHCO3 (10 mL). The organic layer was then dried (MgSO4) and concentrated in vacuo. Flash chromatography of the crude material on silica gel (3:2 EtOAc:hexanes) followed by crystallization (EtOAc/hexanes) afforded (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(2-phenylacetamido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate as a white solid (0.418 g, 69% yield).

後処理

  1. washthe organic layer was washed once with saturated aqueous NaHCO3 (10 mL)
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customFlash chromatography of the crude material on silica gel (3:2 EtOAc:hexanes) followed by crystallization (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-86c347fe3ed14deb9825973aace8fb50
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08334310B2

反応ノート

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