Methanol → [[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phen yl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane

HRID 1913050ノート

反応式

HRID 1913050 の反応式
[Si:1]([O:8][CH2:9][C@H:10]1[O:15][C@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[CH:28][CH:27]=3)[CH:19]=2)([O:16][CH3:17])[C@H:13]([OH:38])[C@@H:12]([OH:39])[C@@H:11]1O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:43](Br)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[CH3:51][OH:52]>CN(C=O)C.O>[CH2:51]([O:52][C@H:11]1[C@H:12]([O:39][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C@@H:13]([O:38][CH2:14][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])=[CH:30][CH:31]=3)[CH:19]=2)([O:16][CH3:17])[O:15][C@@H:10]1[CH2:9][O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C:29]1[CH:28]=[CH:27][CH:26]=[CH:31][CH:30]=1

参加物

7

反応物 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86685148(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxy-methyl]-2-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol

生成物 1

HCID 86685149[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phen yl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

(2S,3R,4S,5S,6R)-6-[(tert-butyl(dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phenyl]methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 7f (2.90 g, 4.78 mmol) was dissolved in 70 mL DMF and cooled to 0° C., followed by addition of 60% NaH (955 mg, 23.9 mmol). The reaction mixture was warmed and stirred for 1 hour at room temperature before benzyl bromide (3.0 mL, 23.9 mmol) was added. After stirring for 3 hours, 5 mL methanol and 10 mL water were added. The reaction mixture was partitioned after 100 mL water and 30 mL saturated sodium chloride solution were added. The aqueous phase was extracted with ethyl acetate (50 mL×3) and the organic extract was washed with saturated sodium chloride solution (30 mL) and combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound [[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[[4-(2,2,2-trifluoroethoxy)phen yl]methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]tert-butyl-dimethyl-silane 7g (4.60 g, pale yellow liquid), which was used directly in the next step without purification.

後処理

  1. temperatureThe reaction mixture was warmed
  2. additionwas added
  3. customThe reaction mixture was partitioned after 100 mL water and 30 mL saturated sodium chloride solution
  4. additionwere added
  5. extractionThe aqueous phase was extracted with ethyl acetate (50 mL×3)
  6. extractionthe organic extract
  7. washwas washed with saturated sodium chloride solution (30 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-6e492f7d52884e50a880a378b84de9b9
出典データセット
uspto-grants-2013_12
特許番号
US08609622B2

反応ノート

読み込み中…