Diethyl Ether → (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one

HRID 1681974ノート

反応式

HRID 1681974 の反応式
[CH2:1]([C@H:7]1[C@@H:12]([OH:13])[CH2:11][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:26]([Si:30]([CH3:33])([CH3:32])Cl)([CH3:29])([CH3:28])[CH3:27].CCOCC>CN(C=O)C>[CH2:1]([C@H:7]1[C@@H:12]([O:13][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:33])[CH3:32])[CH2:11][C@@H:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:9][C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 11013671(3S,4S,6R)-3-Hexyltetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

生成物 1

HCID 22847451(3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy-]6-undecyl-2H-pyran-2-one収率 63.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixture was poured in to 100 ml of ether and washed with 1N hydrochloric acid. The organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There were obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-butyl).

後処理

  1. washwashed with 1N hydrochloric acid
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe material obtained
  6. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-d2118e25524a471b9e5b8a3444aa24e3
出典データセット
uspto-grants-1992_12
特許番号
US05175186

反応ノート

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