Benzyl Bromide → (2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate

HRID 85709ノート

反応式

HRID 85709 の反応式
[OH:1][C@H:2]1[C@H:7]([OH:8])[C@@H:6]([OH:9])[C@H:5]([OH:10])[O:4][C@@H:3]1[C:11]([OH:13])=[O:12].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.Br[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C.CC(O)C.C(Cl)Cl>[OH:1][C@H:2]1[C@H:7]([OH:8])[C@@H:6]([OH:9])[C@H:5]([OH:10])[O:4][C@@H:3]1[C:11]([O:13][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:12]

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 441478beta-D-glucopyranuronic acidHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 58148857(2S,3S,4S,5R,6R)-benzyl 3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylate収率 65%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21966342Isopropanol methylene chloride溶媒

実験手順

To a solution of (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-carboxylic acid (1 g, 5.15 mmol) and TBAF in THF (6.18 mL, 6.18 mmol) in DMF (7 mL) was slowly added (bromomethyl)benzene (0.925 g, 5.41 mmol) at 0° C. The clear solution was warmed up to room temperature slowly and let it stir for 17 hours. TLC indicated the reaction was completed (20% iPrOH/CH2Cl2). The solvent was removed and the reaction residue was purified by silica gel chromatography with 10-20% iPrOH/CH2Cl2 to provide the desired product as a colorless oil (950 mg, 65%). LCMS: m/e 283.31 (M−H)−, 2.55 min (method 10).

後処理

  1. customat 0° C
  2. customThe solvent was removed
  3. customthe reaction residue was purified by silica gel chromatography with 10-20% iPrOH/CH2Cl2

出典と根拠

ORDレコード
ord-936e74c96b654b12b1c7a5f7ca94e20b
出典データセット
uspto-grants-2014_09
特許番号
US08846647B2

反応ノート

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